著者

竹元 万寿美 山本 裕一 阿知波 一雄 James P. Kutney Nikolay M. Stoynov

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集 38 (ISSN:24331856)

巻号頁・発行日

pp.643-648, 1996-09-02 (Released:2017-08-18)

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In recent years, much attention has been paid to the ability of cultured plant cells to transform not only secondary metabolites, but also organic foreign substrates. Therefore, we have studied in the feasibility of using plant cell cultures as the reagents of organic synthesis. In this symposium, we report the synthesis of biologically active com-pounds by using plant cell cultures (N. tabacum, D. carota, C. roseus, P. peltatum) as follows (1) Synthesis of optically active α-phenylpyridylmethanols as organic foreign substrates i) enantioselective reduction of ketone ii) asymmetric hydrolysis of the acetates iii) optically active alcohols production from the corresponding racemates (deracemization of racemates) (2) The efficient synthesis of podophyllotoxin derivatives as starting materials in the clinical anti-cancer drug, Etoposide

著者

森本 俊明 阿知波 一雄 千葉 三男

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集 31 (ISSN:24331856)

巻号頁・発行日

pp.183-189, 1989-09-17 (Released:2017-08-18)

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We found that neutral and cationic rhodium (I) complexes of (S,S)- or (R,R)-MOD-DIOP (1 or 2) showed very high enantio-selectivity in the catalytic asymmetric hydrogenation of α-arylidenesuccinic acid half-esters (3). The optically active α-aryl-methylsuccinic acid half-esters (4) obtained are useful inter-madiates for the synthesis of optically active lignans. Total syntheses of (+)-collinusin (7), (-)-deoxypodophyllotoxin (9), and (+)-neoisostegane (14) were achieved using asymmetric hydrogenation catalyzed by the rhodium(I) complex with (S,S)-MOD-DIOP (2) as a key reaction. Thus, the absolute configurations of natural (+)-collinusin (7) and (+)-neoisostegane (14) were determined to be (R) and (M,6R,7R), respectively. The present asymmetric hydrogenation can provide a practical method for the synthesis of various optically active lignans.

著者

竹元 万寿美 山本 裕一 阿知波 一雄 Kutney James P. Stoynov Nikolay M.

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集

巻号頁・発行日

vol.38, pp.643-648, 1996

---

In recent years, much attention has been paid to the ability of cultured plant cells to transform not only secondary metabolites, but also organic foreign substrates. Therefore, we have studied in the feasibility of using plant cell cultures as the reagents of organic synthesis. In this symposium, we report the synthesis of biologically active com-pounds by using plant cell cultures (N. tabacum, D. carota, C. roseus, P. peltatum) as follows (1) Synthesis of optically active α-phenylpyridylmethanols as organic foreign substrates i) enantioselective reduction of ketone ii) asymmetric hydrolysis of the acetates iii) optically active alcohols production from the corresponding racemates (deracemization of racemates) (2) The efficient synthesis of podophyllotoxin derivatives as starting materials in the clinical anti-cancer drug, Etoposide