Special Issue

James P. Kutney's Special Issues, Vol. 56, No. 1-2, 2002

73 data found. 61 - 73 listedFirst Previous
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 531 - 536
Published online:
DOI: 10.3987/COM-01-S(K)34
A Novel Rearranged Cholestane Glycoside with a δ-Lactone Ring System from Ornithogalum saundersiae Bulbs

Minpei Kuroda, Yoshihiro Mimaki,* Hiroyuki Koshino, and Yutaka Sashida

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


The bulbs of Ornithogalum saundersiae have been revealed to contain a variety of cholestane glycosides. Further chemical investigation of the MeOH extract of O. saundersiae bulbs have resulted in the isolation of a novel 24(23→22)abeo-cholestane glycoside with a δ-lactone system (1). The structure of 1 was elucidated on the basis of extensive spectroscopic analysis and the result of acid hydrolysis.

PDF (71KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 537 - 544
Published online:
DOI: 10.3987/COM-01-S(K)45
Studies on the Constituents of Indonesian Borreria latifolia

Kohei Kamiya, Yasuhiro Fujita, Yasuhisa Saiki, Endang Hanani, Umar Mansur, and Toshiko Satake*

*Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Nishi-ku, Kobe 651-2180, Japan


Seven known iridoid glycosides (1~7), together with one known diterpenoid (8) were isolated from the aerial parts of Borreria latifolia K. Schum. (Rubiaceae) collected in Indonesia, and their structures were identified by spectroscopic methods.

PDF (60KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 545 - 552
Published online:
DOI: 10.3987/COM-01-S(K)51
Chemo-enzymatic Synthesis of Novel β-Amino Acids Substituted by (Thymin-1-yl)methyl Functional Group at the α-Position

Tsutomu Yokomatsu,* Ken Takada, Akihito Yasumoto, Yoko Yuasa, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


A novel β-amino acid having (thymin-1-yl)methyl functionality at the α-position, a useful component of α-substituted β-homoalanyl peptide nucleic acids (β2-PNAs), was synthesized as a protected form from 2-(N3-benzoylthymin-1-yl)methyl-1,3-propanediol via enzymatic desymmetrization catalyzed by lipase PS.

PDF (83KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 553 - 560
Published online:
DOI: 10.3987/COM-01-S(K)55
Model Studies toward Scyphostatin: Synthesis of (S)-4-Benzyl-3-(p-toluenesulfonyl)-2-oxazolidinone and Its Effective Transformation to (S)-N-(1-Benzyl-2-hydroxyethyl)hexadecanamide

Takashi Izuhara, Wakako Yokota, Munenori Inoue, and Tadashi Katoh*

*Sagami Chemical Research Center, NIshi-Ohnuma, Sagamihara, Kanagawa 229-0012, Japan


(S)-4-Benzyl-3-(p-toluenesulfonyl)-2-oxazolidinone (6) was synthesized as a simplified model substrate for the cyclohexenone subunit (2) of scyphostatin (1) starting from L-phenylalanine (3). Transformation of 6 to (S)-N-(1-benzyl-2-hydroxyethyl)hexadecanamide (10) was efficiently achieved to develop a reliable protocol for the construction of the fatty acid-substituted aminopropanol side chain moiety present in 1; the method involves hydrolysis of the cyclic carbamate moiety, N-palmitoylation of the liberated N-Ts-amido function, and removal of the N-Ts protecting group as the crucial steps.

PDF (89KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 561 - 579
Published online:
DOI: 10.3987/COM-01-S(K)58
Aqueous Photolysis of 14C-BAS 654 H under Artificial Sunlight

Mahatam Singh,* Connie Mills, and Dave G. Bolin

*BASF Agro Research Center, 26 Davis Drive, Research Triangle Park, NC 27709, U.S.A.


Photolysis of 14C-BAS 654 H (pyridine and phenyl labels) was conducted in aqueous buffers of pH 5, 7 and 9 at 22 ± 1°C under sterile conditions using artificial sun light source. BAS 654 H degraded photolytically to a number of products as shown in Scheme 3. Identity of the photo degradation products was established employing HPLC co-chromatography with reference standards and/or spectral data (MS and 1H-NMR).

PDF (119KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 581 - 588
Published online:
DOI: 10.3987/COM-01-S(K)66
A Novel Dimeric Lactone Bis-osmundalactone from the Japanese Inedible Mushroom Paxillus atromentosus var. bambusinus

Toshihiro Hashimoto, Takayuki Arakawa, Masami Tanaka, and Yoshinori Asakawa*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-machi, Tokushima, 770-8514, Japan


As a part of our systematic investigation of biologically active substances of inedible mushrooms, we studied the chemical constituents of a Basidiomycetes fungus, Paxillus atrotomentosus var. bambusinus belonging to the Paxillaceae family, and isolated a novel dimeric lactone named bis-osumundalactone (1). The absolute structure of compound (1) was determined by a combination of FAB-MS and high resolution NMR spectra with chemical reactions.

PDF (60KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 589 - 597
Published online:
DOI: 10.3987/COM-01-S(K)67
A Biphenyl, a Dihydrophenanthrene and a Xanthone from Clusia paralycola

Franco Delle Monache,* Giuliano Delle Monache, Bruno Botta, and Eszter Gacs-Baitz

*Centro Chimica Recettori, Università Cattolica, Roma, Italy


A prenylated biphenyl was isolated in a re-examination of the roots of Clusia paralycola and attributed the structure (5a) and the name clusiaparalycoline D for the similarity with other biphenyls isolated from the same source. A second product, isomeric with the previously isolated paralycolin A, was assigned a 9,10-dihydrophenanthrene structure (6a) and named paralycolin B.

PDF (60KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 599 - 605
Published online:
DOI: 10.3987/COM-01-S(K)69
High Pressure Mediated Asymmetric Henry Reaction of Nitromethane with Carbonyl Compounds Catalyzed by Cinchona Alkaloids

Yukihiro Misumi, Robert A. Bulman, and Kiyoshi Matsumoto*

*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan


Asymmetric nitroaldol reactions, catalyzed by cinchona alkaloid, of nitromethane have been investigated. High pressure played an interesting role in the overall reactions that form β-nitro alcohols. From the enantiomeric states of the products formed under different reaction conditions, we deduce that the nature of transition termolecular species formed by the carbonyl compounds with quinidine or quinine determines the stereoselective outcome of the reaction under high pressure.

PDF (37KB)
Note | Special issue | Vol 56, No. 1-2, 2002, pp. 607 - 612
Published online:
DOI: 10.3987/COM-01-S(K)71
Production of Lignans by Haplophyllum patavinum in vivo and in vitro

Lucia Puricelli, Gabbriella Innocenti, Sonia Piacente, Rosy Caniato, Raffaella Filippini, and Elsa M. Cappelletti*

*Dipartimento di Biologia, Università degli Studi di Padova, via Bassi 58/B, 35151 Padova, Italy


Three known arylnaphthalene lignans (justicidin B, diphyllin and tuberculatin), and one dibenzylbutyrolactone (arctigenin) were isolated from native plants, callus and suspension cultures of Haplophyllum patavinum. The present paper represents the first report on arylnaphthalene lignan production by in vitro cultures; in vitro, the biogenetic potential is strictly dependent on the cell strain.

PDF (89KB)
Review | Special issue | Vol 56, No. 1-2, 2002, pp. 613 - 632
Published online:
DOI: 10.3987/REV-01-SR(K)1
Palladium Catalysis in the Construction of the Benzo[b]furan and Furan Rings from Alkynes and Organic Halides or Triflates

Sandro Cacchi,* Giancarlo Fabrizi, and Antonella Goggiomani

*Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185 Roma, Italy


Three general processes leading to the construction of functionalized benzo[b]furan and furan rings are reviewed: 1) the coupling-cyclization methodology, involving the palladium-catalyzed coupling of terminal alkynes with o-iodophenols, or the alternative palladium-catalyzed coupling of terminal alkynes containing proximate oxygen nucleophiles with aryl and vinyl halides or triflates, followed by the cyclization of the resultant coupling intermediates; 2) the oxypalladation-reductive elimination domino reaction, based on the trans addition of the oxygen and an organopalladium complex across the carbon-carbon triple bond, followed by a reductive elimination step; 3) the carbopalladation-cyclization reaction, based on the syn addition of an organopalladium complex, containing an oxygen nucleophile, to the carbon-carbon triple bond, followed by the cyclization of the resultant carbopalladation adduct.

PDF (126KB)
Review | Special issue | Vol 56, No. 1-2, 2002, pp. 633 - 692
Published online:
DOI: 10.3987/REV-01-SR(K)2
Recent Progress in the Chemistry of Polyacylated Anthocyanins as Flower Color Pigments

Toshio Honda* and Norio Saito

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


It is recognized that the bluing effect and stabilization of flower colors will remarkably depend on the number of aromatic acids presented in the polyacylated anthocyanins. Although polyacyl functions would be considered to contribute strongly in the bluing of the flower color at the early stage of the investigation of polyacylated anthocyanin chemistry, the stabilization of flower color is considered to be another important objective by the presence of these aromatic acids at the present time. Since aromatic acids in the polyacylated anthocyanins are obviously linked with the sugar residues through the ester bonds, the polyacylated anthocyanins are classified into seven types by the substitution pattern of acyl functions, and the effect of the stacking structures of polyacyl anthocyanins on the stabilization of the flower color depending on the substitution pattern of acyl groups will be discussed. The physicochemical properties (NMR, UV-VIS spectra) in relation to the stability of the anthocyanins will also be discussed.

Review | Special issue | Vol 56, No. 1-2, 2002, pp. 693 - 709
Published online:
DOI: 10.3987/REV-01-SR(K)3
Benzosultams: Synthesis and Applications

Zhaopeng Liu and Yoshio Takeuchi*

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan


Recent developments on the synthesis and applications of benzosultams are reviewed.

PDF (220KB)
Review | Special issue | Vol 56, No. 1-2, 2002, pp. 711 - 741
Published online:
DOI: 10.3987/REV-01-SR(K)4
Biotransformations of Alkaloids: A Challenge

Wolf-Rainer Abraham* and Grigor Spassov

*GBF - National Research Center for Biotechnology, Research Group Microbial Ecology, Mascheroder Weg 1, D-38124 Braunschweig, Germany


The biotransformation of various alkaloids is reviewed. Special attention is paid to problems in microbial transformations and the different solutions offered by different authors. The biosynthetic potential of the strains selected for biotransformations is compared to the reaction observed in microbal oxidation. An outlook to future developments in other areas, especially from active site modelling, genomics and microbial ecology, are discussed which may contribute to problems in biotransformations.

PDF (234KB)
73 data found. 61 - 73 listedFirst Previous