Special Issue

Yoshio Ban's Special Issues, Vol. 42, No. 1, 1996

61 data found. 31 - 60 listedFirst Previous Next Last
Communication | Special issue | Vol 42, No. 1, 1996, pp. 159 - 164
Published online:
DOI: 10.3987/COM-95-S64
Total Synthesis of Mycalamide A. Further Synthetic Study of the Right Half

Tadashi Nakata, Hideto Fukui, Tadakiyo Nakagawa, and Hiroko Matsukura

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan


The right half 5 of mycalamide A (1) was synthesized starting from (R)- or (S)-pantolactone via the Sharpless asymmetric dihydroxylation as the key step. The total synthesis of mycalamide A (1) was accomplished by coupling of the right and left halves.

PDF (157KB)
Communication | Special issue | Vol 42, No. 1, 1996, pp. 165 - 168
Published online:
DOI: 10.3987/COM-95-S66
Cyclobutane Strategy for the Synthesis of A-Ring Aromatic Trichothecanes

Hideo Nemoto, Junji Miyata, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


A novel synthesis of A-ring aromatic trichothecane (2) by the regiocontrolled cyclization of 5-hydroxy-2-(2-methoxymethoxy-4-methylphenyl)-2-methyl-1-methylidenecyclopentane (10), which was prepared via the 2-phenylcyclobutanone (6) and cyclobutanols (7 and 8) and the 2-methylidene-3-phenylcyclopentanone (9), was achieved.

PDF (89KB)
Communication | Special issue | Vol 42, No. 1, 1996, pp. 169 - 171
Published online:
DOI: 10.3987/COM-95-7139
Lipase AH-Catalyzed Asymmetric Synthesis of (S)-(-)-NB 818

Yukiyoshi Yamazaki and Kazuo Achiwa

*Schol of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan


The first lipase-catalyzed asymmetric synthesis of biologically active (S)-(-)-NB818, has been achieved.

PDF (78KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 173 - 187
Published online:
DOI: 10.3987/COM-94-S1
Synthesis, Conformational Analysis and Biological Evaluation of 2-(5-Deoxy-β-D-ribofuranosyl)pyridine-4-carboxamide

Pieter E. Joos, Alex De Groot, Eddy L. Esmans, Frank C. Alderweireldt, André De Bruyn, Jan Balzarini, and Erik De Clercq

*University of Antwerp (RUCA), Department of Chemistry, Groenenborgerlaan 171, B-2020 Antwerp, Belgium


Coupling of 5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone (5) with 2-lithio-4-(4,5-dihydro-4,4-dimethyloxazol-2-yl)pyridine (6), subsequent mesylation, followed by reduction and ammonolysis resulted in the formation of 2-(5-deoxy-β-D-ribofuranosyl)pyridine-4-carboxamide (4). The anomeric configuration was established with 2D-NOESY-1H-nmr-spectroscopy. Conformational analysis was done with the aid of the high resolution 1H-nmr-spectroscopy data. Compound (4) possessed modest cytostatic activity against a number of tumor cell lines and was slightly inhibitory to vaccinia virus and vesicular stomatitis virus.

PDF (346KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 189 - 194
Published online:
DOI: 10.3987/COM-94-S4-1
Studies on Organometallic Compounds. IX. Synthesis of Bipyridine N-Oxides and Terpyridines by Palladium Catalyzed Cross-Coupling Reaction of Trimethylstannylpyridines with Bromopyridines

Yutaka Yamamoto, Takuo Tanaka, Masayoshi Yagi, and Masayuki Inamoto

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Reaction of trimethylstannylpyridines with bromopyridines in the presence of Pd(PPh3)4 directed toward a practical use was accomplished, giving all nine pyridinylpyridine N-oxides in satisfactory yields. Similarly, nicotelline and 2,2’:6’,2”-terpyridine were produced in good yields.

PDF (140KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 195 - 211
Published online:
DOI: 10.3987/COM-94-S5-1
A Synthesis of the Derivatives of 1,2,3,5,10,10a-Hexahydrobenz[f]indolizine-6,9-dione Having Antifungal Activity as a Simple Model of SaframycinA

Akinori Kubo, Tatsuya Nakai, Yuichi Koizumi, Yoshiyasu Kitahara, Naoki Saito, Yuzuru Mikami, Katsukiyo Yazawa, and Jun Uno

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


A simple and efficient synthesis of 1,2,3,5,10,10a-hexahydrobenz[f] indolizine-6,9-dione (7) and its analogs (28-30) is described starting from the corresponding lactam (15b).

PDF (568KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 213 - 218
Published online:
DOI: 10.3987/COM-94-S6-1
A Convenient Route to the Imidazo[4,5-b]pyridines

Kenichi Harada, Tominari Choshi, Eiichi Sugino, Koichi Sato, and Satoshi Hibino

*Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-02, Japan


The reaction of the acroleins possessing a leaving group, derived from alkenyl sulfides by Vilsmeier reaction, with 4-amino-1-methylimidazole provided a new and convenient route to the imidazo[4,5-b]pyridines, the reaction mechanisms of which were examined by a deuterium labelled experiment.

PDF (209KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 219 - 228
Published online:
DOI: 10.3987/COM-94-S7-1
Syntheses of L-Phenylalanine Derivatives Containing a Sulfur Substituent at the 2-Position

Masashi Ohba, Masaaki Imasho, and Tozo Fujii

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


A full account is given of the chiral syntheses of sulfur-containing L-phenylalanine derivatives (8b,c), selected as key intermediates for the synthesis of models for the starfish alkaloid imbricatine (7), via a 5-step route starting from N,N-diethyl-3,5-dimethoxybenzamide (9). The key steps involve introduction of a sulfur substituent into 9 at the 2-position and construction of the chiral α-amino acid moiety in the chlorides (12b,c) by the “bis-lactim ether” method.

PDF (352KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 229 - 236
Published online:
DOI: 10.3987/COM-95-S10
Practical Total Syntheses of Physostigmines and of Phenserines: A Synopsis

Xue-Feng Pei, Qian-sheng Yu, Bao-yuan Lu, Nigel H. Greig, and Arnold Brossi

*Department of Chemistry, Georgetown University, Washington DC 20057, and Scientist Emeritus NIH, USA


(±)-1,3-Dimethyl-3-cyanomethyl-5-methoxyoxindole (8), or (3S)-enriched 8 obtained by asymmetric alkylation, separated into the optically pure enantiomers (8a) and (8b) when chromatographed on a microcrystalline cellulose triacetate (MCTA) column. Asymmetric alkylation of (±)-1,3-dimethyl-5-tetrahydropyranyloxyoxindole (6) gave the nitrile (9) ((3S) 66 % ee) which could not be separated on the MCTA column. Optically pure eseroline (17a) was obtained by recrystallization of the fumarate salt (66 % ee) obtained from 9 after reduction with Vitride, reductive N-methylation, and treatment with 2N HCl.

PDF (285KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 237 - 240
Published online:
DOI: 10.3987/COM-95-S12
Two New Bisacridone Alkaloids from Citrus Plants1

Motoharu Ju-ichi, Yuko Takemura, Noriko Nagareya, Mitsuo Omura, Chihiro Ito, and Hiroshi Furukawa

*Faculty of Pharmaceutical Science, Mukogawa-Women's University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan


Two new binary acridone alkaloids named citbismine-D (1) and -E (2) were isolated from the roots of Marsh grapefruit (Citrus paradisi). The structures were elucidated by spectroscopic studies as 1 and 2. Citbismine-E (2) was also obtained from the roots of Hirado-Buntan (C. grandis).

PDF (135KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 241 - 250
Published online:
DOI: 10.3987/COM-95-S14
Diastereomeric Preparation of α- and β-Phenylthio Substituted N-Acylpyrazoles

Choji Kashima, Katsumi Takahashi, and Akira Hosomi

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


When 3-phenyl-l-menthopyrazole was used as a chiral auxiliary, the diastereomeric preparation of α- and β-phenylthio-substituted N-acylpyrazoles (4 and 9) was accomplished in high yield by the α-sulfenylation using diphenyl disulfide and the conjugate addition of thiophenol, respectively.

PDF (279KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 251 - 263
Published online:
DOI: 10.3987/COM-95-S15
Synthesi of Aminobenzo[b]pyrrolizinone and Aminobenzo[b]indolizinone Derivatives

Masanao Taga, Hisao Ohtsuka, Isao Inoue, Takayuki Kawaguchi, Sumihiro Nomura, Koichiro Yamada, Tadamasa Date, Hajime Hiramatsu, and Yasuhiko Sato

*Organic Chemistry Research Laboratory, Tanabe Seiyaku Co.Ltd., 2-2-50, Kawagishi, Toddda, Saitama 335-8505, Japan


The fused tricyclic indole derivatives (4a and 4b-1~4b-7) possessing an amino function on the benzo[b]pyrrolizinone or the benzo[b]indolizinone skeleton were synthesized via intramolecular reductive cyclization and Curtius rearrangement, and these compounds exhibited anti-anoxia activity.

PDF (352KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 265 - 272
Published online:
DOI: 10.3987/COM-95-S16
Reaction of 3-Aralkylsulfonyl-2-(N-cyanoimino)-thiazolidines with Oxygen Nucleophiles

Tetsuaki Tanaka, Yumi Nakamoto, Kaori Maekawa, Mayumi Watanabe, Chihiro Nishihara, Chuzo Iwata, and Shuji Uchida

*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


3-Aralkylsulfonyl-2-(N-cyanoimino)thiazolidines react with oxygen nucleophiles, such as sodium alkoxides and carboxylates, at the 3-sulfonyl group to give 3-alkyl- and 3-acyl-2-(N-cyanoimino)thiazolidines, respectively.

PDF (230KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 273 - 280
Published online:
DOI: 10.3987/COM-95-S18
α-Amino Ketone Synthesis from Aldehydes and N-(α-Dialkylaminoalkyl)benzotriazoles

Alan R. Katritzky, Dai Cheng, and Richard P. Musgrave

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, U.S.A.


Thiazolium salt-catalyzed reactions of aldehydes with morpholino-(alkylbenzotriazoles) allow the synthesis of a variety of α-amino ketones. The relationship between reaction conditions and selectivity is discussed.

PDF (244KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 281 - 287
Published online:
DOI: 10.3987/COM-95-S21
The First and Simple Synthesis of Indole Alkaloid, Bipolaramide

Masanori Somei and Toshiya Kawasaki

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


The first and simple total synthesis of bipolaramide was achieved in 31% overall yield from (2S)-2,3-dihydroindole-2-carboxytic acid in three (or two) steps. Derivatives of bipolaramide having halogen, alkenyl, nitro, or azido substituents were also prepared.

PDF (258KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 289 - 304
Published online:
DOI: 10.3987/COM-95-S26
Synthesis of Novel Heterocycle-fused Furo[3,4-d]isoxazoles via Ring Transformation of 2-Isoxazoline-2-oxides by Lewis Acid

Kazuho Harada, Eisuke Kaji, Kuniaki Sasaki, and Shonosuke Zen

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


Reaction of five-membered heterocycle-substituted 2-isoxazoline-2-oxides (2, 3, and 4) with titanium tetrachloride afforded novel heterocycle-fused furo[3,4-d]isoxazoles (5, 6 and 7), respectively. This transformation was applied to indole-substituted 2-isoxazoline-2-oxide (8) to give the corresponding fused furo[3,4-d]isoxazole (9) and indolo[2,3-b]-1-pyrroline-1-oxide (10).

PDF (376KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 305 - 317
Published online:
DOI: 10.3987/COM-95-S35
Enantiopsecific Ring Expansion of Oxetanes: Stereoselective Synthesis of Tetrahydrofurans

Katsuji Ito, Miwa Yoshitake, and Tsutomu Katsuki

*Department of Chemistry, Faculty of Science, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan


Enantiospecific ring expansion of oxetanes to tetrahydrofurans with diazoacetic acid ester was found to be catalyzed by the copper complex of (7R,7’R)-7,7’-di(1-tert-butyldimethylsiloxy-1-methylethyl)-6,6’,7,7’-tetrahydro-5H,5’H-2,2’-bi-1,1’-pyrindine (4). For example, the reaction of (R)-2-phenyloxetane of 89% ee and tert-butyl diazoacetate with Cu-4 complex as a catalyst provided (2S,3R)-tert-butyl 3-phenyltetrahydrofuran-2-carboxylate of 92% ee as a major product, while that of (S)-2-phenyloxetane of 85% ee provided (2S,3S)-tert-butyl 3-phenyltetrahydrofuran-2-carboxylate of 93% ee as a major one.

PDF (339KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 319 - 324
Published online:
DOI: 10.3987/COM-95-S38
Tenuilobine - A New Polyamine Alkaloid from Oncinotis tenuiloba

Martin K. -H. Doll, Armin Guggisberg, and Manfred Hesse

*Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland


A new cross-linked polyamine alkaloid, named tenuilobine (1), was isolated from the leaves of Oncinotis tenuiloba (Apocynaceae), the structure was established by spectroscopic means. It is the first natural alkaloid containing spermine and spermidine as polyamine parts. Presumably, compound (1) is involved in the biosynthesis of the macrocyclic spermidine alkaloids with lactam groups.

PDF (145KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 325 - 331
Published online:
DOI: 10.3987/COM-95-S39
Briarane Diterpenes from Micronesian Gorgonians

Mark T. Hamann, Karl N. Harrison, Anthony R. Carroll, and Paul J. Scheuer

*Department of Chemistry, University of Hawaii at Manoa, 2545 Tha Mall, Honolulu, Hawaii 96822-2275, U.S.A.


Four new briaranes, nui-inoalides A-D, (6-9) are described. They were isolated from octocorals collected in Pohnpei and Ant atoll, Micronesia. The absolute stereochemistry of the known briarane juncin E (5) was determined. Nuiinoalide A (6) and the known gemmacolides A, B, and D (2-4) exhibit immunomodulatory activity.

PDF (190KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 333 - 339
Published online:
DOI: 10.3987/COM-95-S41
Hetericyclization of 5-Trifluoroacetyltricyclo-[,8]undecan-4-one to Some 6- and 7-Membered Nitrogen Heterocycles

Shoji Eguchi, Akira Umada, and Takashi Okano

*Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


Heterocyclization study of 5-trifluoroacetyl[,8]undecan-4-one into pyrimidine, pyridine, and 1,4-diazepine derivatives as a route to trifluoromethylated homoadamantanefused 6- and 7-membered nitrogen heterocycles is reported.

PDF (226KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 341 - 346
Published online:
DOI: 10.3987/COM-95-S42
Effect of Bromides on the Anomalous Photoarylation of 5-Halo-1,3-dimethyluracils

Koh-ichi Seki, Kazue Ohkura, Yuki Fukai, and Masanao Terashima

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


Photolysis of 5-chloro- and 5-fluoro-1,3-dimethyluracil in toluene in the presence of a bromide (e.g.,p-dibromobenzene, 1,2-dibromoethane, and benzyl bromide) and an acid (hifluoroacetic acid, HBr) afforded 1,3-dimethyl-5-tolyluracils and the 6-isomers as the isomeric mixture. 5-Arylation occurred most favorably at ortho, while meta-isomers were preferential products in 6-arylation. The 5-isomers are suggested to be derived from uracils excited in the singlet states, while the 6-isomers are presumed to result from the uracils excited in the triplet states.

PDF (169KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 347 - 358
Published online:
DOI: 10.3987/COM-95-S44
Asymmetric Pictet-Spengler Reaction Using α-Methylbenzylamine as a Chiral Auxiliary Group

Than Soe, Tomohiko Kawate, Naoko Fukui, Tohru Hino, and Masako Nakagawa

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


The Pictet-Spengler reaction of chiral N-(β-3-indolyl)ethyl-α-methylbenzylamine with aldehydes in the presence of acids in refluxing benzene provided 1-substituted tetrahydro-β-carbolines (~72 % de).

PDF (340KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 359 - 374
Published online:
DOI: 10.3987/COM-95-S45
Total Synthesis of the Major Metabolites of Gomisin A. Synthesis of Homochiral Met A-II, Met A-III, and Met F

Masahide Tanaka, Hiroshi Mitsuhashi, Masao Maruno, and Takeshi Wakamatsu

*Central Research Laboratory, Tsumura & Co., 3586 Yoshiwara, Ami-machi, Inashiki-gun, Ibaraki, 300-11, Japan


The total syntheses of the metabolites of gomisin A (1) were achieved. By the Mukaiyama hydration or the successive double bond migration, lactone ring reduction, glycol formation, and reduction, the homochiral lactones (10a-c) provided met A-III (3), A-II (2), D (5), and F (7).

PDF (531KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 375 - 384
Published online:
DOI: 10.3987/COM-95-S49
Synthesis of 5-Substituted Pyrimidine Nucleosides through a Palladium-catalyzed Cross-Coupling of Alkenylhalosilanes

Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, and Tamejiro Hiyama

*Research Laboratory of Resources Utilization, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan


Palladium-catalyzed cross-coupling of alkenylhalosilanes with 5-iodouracil and 5-iodouridine derivatives was described. 5-Iodo-1,3-dimethyluracil coupled with alkenylfluorodimethylsilanes to give the corresponding cross-coupled products in good yield. Fully protected 5-iodo-2’-deoxyuridine derivative also underwent the cross-coupling reaction. Noteworthy is that unprotected 5-iodo-2’-deoxyuridine could be converted into the corresponding cross-coupled products in good yields using alkenyl(difluoro)methylsilanes.

PDF (258KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 385 - 395
Published online:
DOI: 10.3987/COM-95-S50
New Anionic Cyclization of 4- and 5-Alkynylamines: Synthesis of 2-Benzylidene Pyrrolidines and Piperidines

Masao Tokuda, Hirotake Fujita, Makoto Nitta, and Hiroshi Suginome

*Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan


Treatment of 4- and 5-alkynylamines with 0.5-1.2 equiv. of butyllithium brought about a facile anionic cyclization, giving the corresponding enamine pyrrolidines and piperidines having an exo double bond in high yields. Treatment of 4-alkynamides with lithium aluminum hydride also gave the similar enamine pyrrolidines in high yields.

PDF (350KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 397 - 414
Published online:
DOI: 10.3987/COM-95-S55
Total Syntheses of BE-12406 A and Its C(8)-Vinyl Analog

Takamitsu Hosoya, Eiji Takashiro, Yasuko Yamamoto, Takashi Matsumoto, and Keisuke Suzuki

*Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku, Yokohama 223-8522, Japan


Total syntheses of BE-12406 A (3a) and its C(8)-vinyl analog (3c) are described. The key step is the selective O-glycosylation of naphthol (4)with L-rhamnopyranosyl fluoride (5) by employing Cp2HfCl2-AgClO4 in fluorobenzene at -20°C in the presence of a hindered base, 2,6-di-t-butyl-4-methylpyridine (12), affording O-glycoside (11) in good yield.

PDF (695KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 415 - 422
Published online:
DOI: 10.3987/COM-95-S60
Preparation of Optically Active 8,8’-Disubstituted 1,1’-Biisoquinoline

Ken-ichi Hirao, Ryuta Tsuchiya, Yasuhiro Yano, and Hirohito Tsue

*Laboratory of Organic Chemistry, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan


Synhesis of 1,1’-biisoquinolines having substituents in the 8,8’-positions and their resolution by hplc on a chiral column on a preparative scale are described.

PDF (215KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 423 - 435
Published online:
DOI: 10.3987/COM-95-S67
Enantioselective [2,3]-Wittig Rearrangement via a Chiral Boron Ester Enolate

Katsuhiko Fujimoto, Chiho Matsuhashi, and Takeshi Nakai

*Department of Chemical Technology, Faculty of Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan


The first enantioselective [2,3]-Wittig rearrangement of α-(allyloxy)- acetates is described which involves a chiral boron enolate with a chiral bis-sulfonamide ligand to afford the α-hydroxy-β-alkyl-γ,δ-unsaturated esters in a high enantioselectivity (>95%ee), along with a high threo diastereoselectivity.

PDF (439KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 437 - 443
Published online:
DOI: 10.3987/COM-95-S69
The Synthesis of 1β-Fluorocarbapenem Derivative

Masataka Ihara, Ken Satoh, Yohhei Ishida, Nobuaki Taniguchi, Yuji Tokunaga, Makoto Takemura, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The synthesis of 1β-fluorocarbapenem derivative (16) was carried out starting with the 4-acetoxyazetidin-2-one (3) through the carbapenem formation utilizing the Sankyo’s procedure.

PDF (237KB)
Paper | Special issue | Vol 42, No. 1, 1996, pp. 445 - 451
Published online:
DOI: 10.3987/COM-95-S70
Aloxylation at Meta Position to Hydroxyl Group of L-Tyrosine: Preparation of Alkyl (S)-2,4-Dialkoxyphenylalaninates

Hiroshi Hara, Tsutomu Inoue, Masaki Endoh, Hiroshi Nakamura, Hiroyuki Takahashi, and Osamu Hoshino

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 12, Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan


Treatment of dienone lactone (2), derived from L-tyrosine, with methanol in the presence of boron trifluoride etherate gave methyl N-protected (S)-2,4-dimethoxyphenylalaninate (4) in 76 % yield. Similarly, two homologues (9 and 10) were conventionally produced from 2.

PDF (178KB)
61 data found. 31 - 60 listedFirst Previous Next Last