NEW OLEFINIC CYCLIZATIONS BY OXYMETALATION - CONVERSION OF (-)-ELEMOL TO (-)-SELINA-4-ALPHA, 11-DIOL (CRYPTOMERIDIOL) AND (-)-GUAI-1 (10)-ENE-4-ALPHA, 11-DIOL

被引：22

作者：

RENOLD, W ^{[1
]}

OHLOFF, G ^{[1
]}

NORIN, T ^{[1
]}

机构：

[1] ROYAL INST TECHNOL,DEPT ORGAN CHEM,S-10044 STOCKHOLM 70,SWEDEN

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 04期

关键词：

D O I：

10.1002/hlca.19790620409

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Acetoxythallation of (−)‐elemol acetate (1b) yields a diacetate 2b which after treatment with lithium aluminium hydride gives (−)‐guai‐1 (10)‐ene‐4α, 11‐diol (2a). (−)‐Elemol (1a) is converted to (−)‐selina‐4α, 11‐diol (9, cryptomeridiol) by hydroxymercuration followed by reductive demercuration. (+)‐γg‐Elemene (5) similarly yields (+)‐selin‐7(11)‐en‐4α‐ol (11, juniper camphor). The stereochemistry and mechanism of these metal salt‐induced olefinic cyclization and their biogenetic implication are discussed. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：985 / 993

页数：9

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