CONFORMATIONAL DIFFERENCE BETWEEN ERYTHRINAN-3-ONES AND HOMOERYTHRINAN-3-ONES - TOTAL SYNTHESIS OF (+/-)-SCHELHAMMERIDINE AND (+/-)-3-EPISCHELHAMMERIDINE

被引：8

作者：

TSUDA, Y

HOSOI, S

MURATA, M

机构：

[1] Faculty of Pharmaceutical Sciences, Kanazawa University, Kanazawa, 920

来源：

HETEROCYCLES | 1990年 / 30卷 / 01期

关键词：

D O I：

10.3987/COM-89-S49

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Erythrinan- and homoerythrinan-3-ones behave differently toward hydride reductions suggesting their conformational difference: for example, Δ1-erythrinan-3-one gives 3α-alcohol and Δ1-homoerythrinan-3-one gives 3β-alcohol stereoselectively on reduction with NaBH4-CeCl3 in methanol. Based on these observations, total syntheses of homoerythrinan alkaloids, schelhammeridine and 3-epischelhammeridine, and an erythrinan alkaloid, 8-oxoerysotrine, were accomplished. © 1990.

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页码：311 / 316

页数：6

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