Special Issue

Satoshi Omura's Special Issues, Vol. 69, No. 1, 2006

57 data found. 1 - 30 listed Next Last
Preface | Special issue | Vol 69, No. 1, 2006, pp. 1 - 3
Published online:
DOI: 10.3987/2006-69-0001
In Honor of Professor Satoshi Omura on the Occation of His 70th Birthday

Takeshi Kitahara

*Professor Emeritus, the University of Tokyo
Guest Professor, Kitasato University
Head, The Kitasato Institute
Professor, Teikyo Heisei University

Curriculum vitae | Special issue | Vol 69, No. 1, 2006, pp. 5 - 6
Published online:
DOI: 10.3987/2006-69-0005
Biographical Data

Satoshi Ōmura*

*Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642, Japan

Publications | Special issue | Vol 69, No. 1, 2006, pp. 7 - 42
Published online:
DOI: 10.3987/2006-69-0007
Publications List

Satoshi Ōmura*

*Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642, Japan

Communication | Special issue | Vol 69, No. 1, 2006, pp. 43 - 48
Published online: 7th March, 2006
DOI: 10.3987/COM-06-S(O)4
3,4,5,6-Tetrasubstituted 2-Pyridone Synthesis via Nucleophilic Addition of Active Methine Compounds to Dialkynyl Imines Directed to the Synthesis of (-)-A58365A

Iwao Hachiya, Shiho Fukushima, and Makoto Shimizu*

*Department of Chemistry for Materials, Mie University, Tsu, Mie 514-8507, Japan


3,4,5,6-Tetrasubstituted-2-pyridone synthesis via nucleophilic addition of active methine compounds to dialkynyl imines directed to the synthesis of (-)-A58365A has been developed. The reaction of active methine compounds such as malonic esters or β-keto esters to dialkynyl imines provided 3,4,5,6-tetrasubstituted-2-pyridones in moderate to good yields.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 49 - 54
Published online: 28th April, 2006
DOI: 10.3987/COM-06-S(O)5
Total Synthesis of (—)-Pramanicin

Shin-ya Aoki, Taro Tsukude, Yukari Miyazaki, Ken-ichi Takao, and Kin-ichi Tadano*

*Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan


The total synthesis of natural (-)-pramanicin, a highly oxygenated γ-lactam-type antifungal agent, is described. The enantiospecific total synthesis of this natural product commenced with 5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose as an enantiopure starting material.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 55 - 61
Published online: 16th May, 2006
DOI: 10.3987/COM-06-S(O)7
Rapid ‘SAR’ via Click Chemistry: An Alkyne-Bearing Spiramycin is fused with Diverse Azides to Yield New Triazole-Antibacterial Candidates

Tomoyasu Hirose, Toshiaki Sunazuka, Yoshihiko Noguchi, Yukie Yamaguchi, Hideaki Hanaki, K. Barry Sharpless, and Satoshi Omura*

*Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642,


The spiramycin analogue, 2’-acetyl-4’’’-de-N-methyl-4’’-O-t- butyldimethylsilylspiramycin I 3,18-(O-t-butyldimethylsilyl)acetal(1), was found to be an adequate antibacterial agent against MRSA strains. An acetylenic sidechain was attached to 1 producing the analog (8), with the core intact but displaying a tethered terminal alkyne, ready for reaction with 19 diverse azides. In the event, the copper-catalyzed Fokin-Huisgen triazole synthesis/coupling gave each of the nineteen new 4’’-O-acyl triazole derivatives of 1 in good to nearly quantitative isolated yields.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 63 - 67
Published online: 20th June, 2006
DOI: 10.3987/COM-06-S(O)11
Synthesis of Tulipalin B and 1-O-Methyl-6-tuliposide B

Kengo Shigetomi, Takao Kishimoto, Kazuaki Shoji, and Makoto Ubukata*

*Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Sapporo 060-8589,Japan


Toward the total synthesis of 6-tuliposide B, facile synthesis of tulipalin B and 1-O-methyl-6-tuliposide B (Methyl 6-O-((S)-3’,4’-dihydroxy-2’- methylenebutanoyl)-β-D-glucopyranoside) has been achieved.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 69 - 72
Published online: 20th June, 2006
DOI: 10.3987/COM-06-S(O)14
Stereoselective Synthesis of trans-3a-Aryloctahydroindoles Using Cyclization of N-Vinylic α-(Methylthio)acetamides

Miho Saito, Jun-ichi Matsuo, Masahiko Uchiyama, and Hiroyuki Ishibashi*

*Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kanazawa 920-1192, Japan


Treatment of N-(2-arylcyclohex-1-enyl)-α-(methylthio)acetamide with NCS underwent cyclization to give 3a-arylhexahydroindol-2-one, which was stereoselectively converted into trans-3a-aryloctahydroindole.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 73 - 81
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-S(O)18
Acridone Heterocycles as Fluorescent Sensors for Anions

M. Teresa Blázquez, Francisco M. Muñiz, Silvia Sáez, Luis M. Simón, Ángel Alonso, César Raposo, Anna Lithgow, Victoria Alcázar, and Joaquín R. Morán*

*Organic Chemistry Department, University of Salamanca, Plaza de los Caídos 1-5, Salamanca E-37008, Spain


An acridone heterocycle with a suitable functionalization can be used as a fluorescent sensor for anions. Large differences in fluorescence efficiency are observed when chlorides are associated in the receptor cavity. Chlorides form two different complexes in chloroform, with 2:1 and 1:1 stoichiometries. The combined presence of receptor (1) and 18-crown-6 ether allows the extraction of aqueous α-amino acids to the chloroform phase. This extraction is very sensitive to temperature.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 83 - 89
Published online: 21st July, 2006
DOI: 10.3987/COM-06-S(O)22
Direct Observation of ESR Spectra of Bicyclic Nine-Membered Enediynes at Ambient Temperature

Masahiro Hirama,* Kimio Akiyama,* Parthasarathi Das, Takashi Mita, Martin J. Lear, Kyo-ichiro Iida, Itaru Sato, Fumihiko Yoshimura, Toyonobu Usuki, and Shozo Tero-Kubota

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan


The ESR spectra for synthetic bicyclo[7.3.0]epoxydodecadienediynes in solution at room temperature are steady. These spectra originate from the Masamune-Bergman cyclization of bicyclo[7.3.0]epoxydodecadienediynes to p-benzyne biradicals and the equilibrium between the two forms. Comparison of the ESR spectra of the unlabeled and 13C-labeled nine-membered enediynes indicated that the spectra are not directly due to the p-benzyne biradicals but rather to more stable secondary radical intermediates.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 91 - 98
Published online: 21st July, 2006
DOI: 10.3987/COM-06-S(O)23
Convergent Synthesis of the CDEF Ring Fragment of Yessotoxin via α-Cyano Ethers

Tohru Oishi,* Miho Suzuki, Koji Watanabe, and Michio Murata

*Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan


The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)3 to afford the α-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 99 - 105
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-S(O)30
4-Aryl-2-quinolones via a Domino Heck Reaction / Cyclization Process

Roberta Bernini, Sandro Cacchi,* Giancarlo Fabrizi,* and Alessio Sferrazza

*Department of Studies of Chemistry and Technology of Biologically Active Substances, University “La Sapienza”, P. le A. Moro 5, 00185 Rome, Italy


The reaction of methyl β-(o-acetamidophenyl)acrylates with aryl iodides in the presence of Pd(OAc)2 and KOAc in DMF at 120 °C affords 4-aryl-2-quinolones in allowable to good yields.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 107 - 111
Published online: 25th August, 2006
DOI: 10.3987/COM-06-S(O)44
Synthesis of Cyclic Polyglycerols

Takahiro Kawagishi, Kimio Yoshikawa, Makoto Ubukata, Masahiro Hamada, and Noriyuki Nakajima*

*Biotechnology Research Center, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan


Authentic standards of cyclic polyglycerol, with well-defined structures and degrees of polymerization from 3 to 6 cyclic oligomers, have been efficiently synthesized. The intramolecular cyclization conditions gave cyclic glycerols more effectively than intermolecular coupling conditions.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 113 - 118
Published online: 25th August, 2006
DOI: 10.3987/COM-06-S(O)39
Oxidative Cyclization of Isodityrosine Tripeptides: Optimized Condition and Application of Electrochemically Generated Thallium(III) Ion

Takamasa Tanabe, Rika Obata, and Shigeru Nishiyama*

*Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan


Thallium(III) trinitrate oxidation of the tripeptide, which was a synthetic precursor of the 17-membered isodityrosine natural product, eurypamide, was investigated to give the desired cyclized compound in 96% yield at best. In addition, the thallium(III) species generated by electrochemical oxidation of thallium(I) successfully produced the target compounds.

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Communication | Special issue | Vol 69, No. 1, 2006, pp. 119 - 122
Published online: 27th October, 2006
DOI: 10.3987/COM-06-S(O)48
Reaction of 2H-Cyclohepta[b]furan-2-ones with Pyridinium Salts of Trifluoromethanesulfonic Anhydride

Noboru Morita,* Tomohiro Matsuki, Masashi Nakashima, Taku Shoji, Kozo Toyota, Shigeru Kikuchi, and Shunji Ito

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan


2H-Cyclohepta[b]furan-2-one (1) reacted with TPT, electrophilically to give 3-dihydropyridinyl-2H-cyclohepta[b]furan-2-one and subsequent treatment with sodium hydroxide in ethanol gave 3-(4-pyridinyl)-2H-cyclohepta[b]furan- 2-one in excellent yields. Furthermore, it reacted with methyl iodide give a corresponding pyridinium salt easily.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 123 - 132
Published online: 27th January, 2006
DOI: 10.3987/COM-05-S(O)1
5-Acyl-2H-pyran-2-ones in the Schmidt Reaction: Migration of the Pyran-2-one Ring

Franc Pozgan, Maja Krejan, Slovenko Polanc, and Marijan Kočevar*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, SI-1000 Ljubljana, Slovenia


The Schmidt reaction of the 5-acyl-2H-pyran-2-ones (1af) using NaN3/H2SO4 was investigated. The reaction proceeded with complete regioselectivity in the 5-acetyl series to give the corresponding 5-acetylamino derivatives (2ac) via pyran-2-one ring migration. In contrast, the reaction applied to the 5-benzoyl-2H-pyran-2-ones (1df) led to the formation of both regioisomers, (2df) and (3df). The latter resulted from the phenyl shift in this reaction and were obtained as minor products. The 3,5-diacylamino-2H-pyran-2-ones (2a) and (2d) were selectively debenzoylated at position 3.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 133 - 149
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-S(O)2
Starter Unit Specificity of the Asukamycin “Upper” Chain Polyketide Synthase and the Branched-Chain Fatty Acid Synthase of Streptomyces nodosus subsp. asukaensis

Yiding Hu and Heinz G. Floss*

*Department of Chemistry, University of Washington, Seattle, WA 98195-1700, U.S.A.


Asukamycin, a member of the manumycin family of antibiotics, obtained from Streptomyces nodosus subsp. asukaensis, contains two amide-linked polyketide chains, one of which, the “upper” chain, is initiated by cyclohexanecarboxylic acid as the starter unit. Analysis of the congeners of asukamycin present in the fermentation and of the fatty acid spectrum of the mycelial lipids revealed that the “upper” chain polyketide synthase (PKS) and the branched-chain fatty acid synthase (FAS) of S. nodosus ssp. asukaensis share qualitatively, although not quantitatively, the same starter unit selectivity for branched chain and alicyclic carboxylic acids. Feeding of various alicyclic carboxylic acids of different ring size resulted in the formation of new asukamycin analogs as well as changes in the fatty acid spectrum. Feeding of various alicyclic carboxylic acids also shut off the endogenous production of cyclohexanecarboxylic acid.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 151 - 166
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-S(O)3
Exploring the Synthesis of Masked Phosphoramido 6-Vinylcytidine Derivatives as Building Blocks for Cross-Linking Oligonucleotides

Marco Radi, Raffaella Spinosa, Maria Cristina Parlato, Federico Corelli, and Maurizio Botta*

*Department of Medicinal Chemistry, University of Siena, Via Aldo Moro, 53100 Siena, Italy


In the present work the synthesis of building blocks (2a,b), bearing a masked form of the reactive vinyl group bound to the C-6 position of a cytidine derivative, has been studied. The understanding of byproduct formation together with conformational considerations let us to plan a straightforward approach for the synthesis of the target compounds.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 167 - 178
Published online: 12th May, 2006
DOI: 10.3987/COM-06-S(O)6
Reactions of 8-(Triphenylphosphoimino)quinoline with Aryl Aldehydes and Aryl Isocyanates: Formation of 2-Aryl-4H-imidazo[4,5,1-ij]quinolines and Related Systems

Kentaro Nagamatsu, Erina Akiyoshi, Hidenori Ito, Hiroyuki Fujii, Akikazu Kakehi, and Noritaka Abe*

*Department of Chemistry, Faculty of Science, Yamaguchi University, Yoshida, Yamaguchi 753-8512, Japan


The reaction of 8-(triphenylphosphoimino)quinoline with aryl aldehydes gave 2-aryl-4H-imidazo[4,5,1-ij]quinolines. In the reaction, tandem aza-Wittig reaction and cyclization attended with hydride shift occurred. The reaction of 8-(triphenylphosphoimino)quinoline with aryl isocyanates gave 1,3-diaryl-1,2,3,9a-tetrahydro[1,3,5]triazolo[2’,3’:2,1;3’,4’-a]imidazo[4,5,1-ij]quinolin-2-ones (11) and 2-(arylamino)imidazo[4,5,1- ij]quinolin-4(4H)-ones (12). The structures of 11a (Ar = Ph) and 12a (Ar = Ph) were confirmed by X-Ray structure analyses.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 179 - 192
Published online: 23rd May, 2006
DOI: 10.3987/COM-06-S(O)8
Synthesis of New Pyrrolidine Derivatives as Inhibitors of α-Mannosidase and of the Growth of Human Glioblastoma Cells

Sylvain Favre, Hélène Fiaux, Catherine Schütz, Pierre Vogel, Lucienne Juillerat-Jeanneret,* and Sandrine Gerber-Lemaire*

*Laboratory of Glycochemistry and Asymmetric Synthesis, Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime (BCH), CH-1015 Lausanne, Switzerland


New 2-benzylamino-3,4-dihydroxypyrrolidines bearing aromatic and aliphatic amido side chains have been prepared. The influence of the amido substituents on the inhibitory activity of these diamines toward 24 commercially available glycosidases was determined. The most potent and selective α-mannosidase inhibitor (6d) (N-[(2R)-2-({[(2R,3R,4S)-3,4-dihydroxypyrrolidin -2-yl]methyl} amino)-2-phenylethyl]-3-bromobenzamide) of these series was also the most potent inhibitor of the growth of human glioblastoma cells.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 193 - 216
Published online: 23rd May, 2006
DOI: 10.3987/COM-06-S(O)9
Novel Chiral Synthetic Path to Indolizidine and Quinolizidine Alkaloids by Means of a Samarium Diiodide-Promoted Reductive Carbon-Nitrogen Cleavage Reaction: Synthesis of (+)-(8R, 8aR)-Perhydro-8-indolizidinol and (—)-Deoxynupharidine

Miho Katoh, Hirotake Mizutani, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan


Novel chiral synthetic procedures for indolizidine and quinolizidine alkaloids were developed, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was employed as a key step. Application of the procedure led to the total synthesis of (+)-(8R, 8aR)-perhydro-8-indolizidinol and (-)-deoxynupharidine.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 217 - 222
Published online: 20th June, 2006
DOI: 10.3987/COM-06-S(O)10
Syntheses of Ulocladol

Hitoshi Abe,* Tomoko Fukumoto, Keisuke Nishioka, Masatsugu Arai, Yasuo Takeuchi, and Takashi Harayama

*Faculty of Pharmaceutical Sciences, Okayama University, Okayama 700-8530, Japan


Several synthetic routes to produce ulocladol were established through a short-step transformation involving the selective demethylation or a lactone transformation process.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 223 - 229
Published online: 28th July, 2006
DOI: 10.3987/COM-06-S(O)16
Three New Phlegmarine-Type Lycopodium Alkaloids, Lycoposerramines-X, -Y and -Z, Having a Nitrone Residue, from Lycopodium serratum

Kazuaki Katakawa, Mariko Kitajima, Kentaro Yamaguchi, and Hiromitsu Takayama*

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Three new phlegmarine-type Lycopodium alkaloids, lycoposerramines-X (2), -Y (3), and -Z (5), having a nitrone residue were isolated from the club moss Lycopodium serratum Thunb. The structures of these new alkaloids, together with the stereostructures of the related alkaloids, huperzines J (1) and K (4), were elucidated by spectroscopic analyses.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 231 - 237
Published online: 1st August, 2006
DOI: 10.3987/COM-06-S(O)20
Further Structure-Activity Relationships of the Myxobacterial Antibiotics Cystothiazoles

Bangi A. Kundim, Jianhua Qi, Ryosuke Fudou, Shigeru Yamanaka, and Makoto Ojika*

*Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan


Eight derivatives of the bithiazole-type myxobacterial antibiotic cystothiazole A were evaluated for antifungal activity against a phytopathogenic microorganism for a further structure-activity relationship. Two of them, an acetate and a fully conjugated non-chiral derivative, were new derivatives obtained by chemical derivatization of cystothiazole C. The results confirmed the importance of the bend conformation at C-4/C-5, the methyl ether at C-5, and the lipophilicity of the terminal alkyl group of the molecule.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 239 - 251
Published online: 18th August, 2006
DOI: 10.3987/COM-06-S(O)24
Anthocyanins from the Rhizome of Raphanus sativus, and Change in the Composition during Maturation

Mihoko Mori, Shuji Nakagawa, Masayoshi Maeshima, Satoshi Niikura, and Kumi Yoshida*

*Graduate School of Information Science, Nagoya University, Chikusa, Nagoya 464-8601, Japan


Four new acylated anthocyanins with three known pigments were isolated from the rhizome of the Chinese red radish (Raphanus sativus cv. Beijing hong xin), and their structures were determined. All of them possessed pelargonidin 3-sophoroside-5-glucoside as a common structure, and each was substituted with one to two aromatic acyl residues, with/without a malonyl residue and with/without a sugar residue. The major aromatic acyl moiety was feruloyl. Most of the pigments were malonylated. The cambium part was richer in polyacylated anthocyanins than the parenchyma part.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 253 - 258
Published online: 28th July, 2006
DOI: 10.3987/COM-06-S(O)25
Chaxine A, an Osteoclast-Forming Suppressing Substance, from the Mushroom Agrocybe chaxingu

Hirokazu Kawagishi,* Takuto Akachi, Tetsuhiro Ogawa, Kikuko Masuda, Kohji Yamaguchi, Kazunaga Yazawa, and Mamoru Takahashi

*Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan


A novel compound, chaxine A, (1), and a known one (2) were isolated from the mushroom Agrocybe chaxingu. These compounds suppressed the formation of osteoclast.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 259 - 269
Published online: 11th August, 2006
DOI: 10.3987/COM-06-S(O)26
1-Hydroxyyohimbine and Its Derivatives: New Potent α2-Blockers for the Treatment of Erectile Dysfunction

Masanori Somei,* Koichi Noguchi, Katsumasa Yoshino, Koichiro Mori, Mamiko Asada, Fumio Yamada, Yoshio Tanaka, Koki Shigenobu, and Katsuo Koike

*Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan


1-Hydroxyyohimbine and its various derivatives are prepared for the first time. These novel compounds are found to be potent α2-blockers comparable to yohimbine itself.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 271 - 282
Published online: 22nd August, 2006
DOI: 10.3987/COM-06-S(O)27
A New Useful Conversion Method of Naltrexone to 14-Deoxynaltrexone

Yumiko Osa, Yoshihiro Ida, Yumiko Yano, Kimio Furuhata, and Hiroshi Nagase*

*School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan


A novel synthetic method of 14-deoxynaltrexone (2), a μ-opioid receptor antagonist possessing a new message-structural part of opioid ligands, was established. Naltrexone methyl ether (5) was first converted to its acetal (24), followed by dehydration with thionyl chloride in pyridine to afford 8,14-dehydroderivative (26) of 24. The resulting unsaturated compound (26) was reduced with PtO2 under hydrogen to give saturated compound (27), which was then acid-hydrolyzed to afford the desired 14-deoxynaltrexone (23) (3-O-methyl of 2) without degradation of the naltrexone skeleton. The total yield from naltrexone (1) to 23 was 86%. Finally, 23 was demethylated to give 14-deoxynaltrexone (2) in 85% yield. This method provides a useful reaction route to give various important intermediates as a message part to synthesize selective ligands for the opioid receptor subtypes.

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 283 - 294
Published online: 28th July, 2006
DOI: 10.3987/COM-06-S(O)28
Synthesis of Functionalized Phospholane Oxides and Phosphorinane Oxides from 1,4- and 1,5-Di-O-mesyloxy Compounds

Tadashi Hanaya,* Karsten Schürrle, and Hiroshi Yamamoto

*Department of Chemistry, Faculty of Science, Okayama University, Tsushima-naka, Okayama 700-8530, Japan


Treatment of 1,4-di-O-mesyl-2,3-di-O-methyl-L-threitol (8b) with phenylphosphine in the presence of sodium hydride in DMSO, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane 1- oxide (7), while the same treatment of 1,5-di-O-mesyl-2,3,4-tri-O-methyl-meso- xylitol (11b) provided 2,3,4-trimethoxy-1-phenylphosphorinane 1-oxide (14).

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Paper | Special issue | Vol 69, No. 1, 2006, pp. 295 - 301
Published online: 22nd September, 2006
DOI: 10.3987/COM-06-S(O)33
Arabidopside F, a New Oxylipin from Arabidopsis thaliana

Haruyuki Nakajyo, Yosuke Hisamatsu, Mitsuhiro Sekiguchi, Nobuharu Goto, Koji Hasegawa, and Hideyuki Shigemori*

*Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba 305-8572, Japan


A new oxylipin, arabidopside F (1) was isolated from the aerial parts of Arabidopsis thaliana, together with MGDG-O (2), arabidopsides A (3) and B (4). The structure of arabidopside F (1) was elucidated by spectroscopic data and chemical means. Arabidopside F (1) was a rare monogalactosyl diacylglyceride containing dinor-oxophytodienoic acid and 1 exhibited inhibitory effects on the growth of the root of cress (Lepidium sativum L.) seedlings at 5x10-5 mol/L.

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57 data found. 1 - 30 listed Next Last