Unusual boron trifluoride-catalyzed reactions of taxinine derivatives with α- and β-4(20)-epoxides

被引：9

作者：

Hosoyama, H ^{[1
]}

Shigemori, H ^{[1
]}

Kobayashi, J ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 11期

关键词：

boron and compounds; epoxides; rearrangements; taxoids;

D O I：

10.1016/S0040-4039(99)00135-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boron trifluoride-catalyzed reaction of beta-4(20)-epoxy-5-O-triethylsilyltaxinine A (1) gave the 3,5-diene (3) and the 3,8-cyclopropane (4) derivatives, while the similar reaction of the corresponding alpha-4(20)-epoxide (2) afforded the ring contracted derivative (5) and its hemiacetal dimer (6). Plausible mechanisms of these reactions containing 1,2-hydride shift (3 and 4 from 1) or pinacol-type rearrangement (5 and 6 from 2) are proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2149 / 2152

页数：4

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