- 著者
- 山中 悦二 丸田 悦子 笠松 里江 相見 則郎 坂井 進一郎 / / TANOMJIT SUPAVITA J. DAVID PHILLIPSON
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.34, no.9, pp.3713-3721, 1986-09-25 (Released:2008-03-31)
- 参考文献数
- 21
- 被引用文献数
- 4 6
Oxidation of the enamine (6) with dibenzoyl peroxide followed by reduction with NaBH4 gave the benzoate (8), which was converted to the cis-hydroxyl compound (9), while hydroboration-oxidation of 6 gave the trans-isomer (11). Treatment of a mixture of the enamines (13 and 14) with dibenzoyl peroxide/NaBH4 gave the benzoates (15 and 16), which were converted to 14α-hydroxy-3-isorauniticine (17) and the acetal (18), respectively. Hydroboration-oxidation of 13 gave 14α-hydroxyrauniticine (2), which was found to be identical with the natural alkaloid whose structure had erroneously been proposed as 14β-hydroxy-3-isorauniticine (4).