BEYERANE DITERPENES - STRUCTURE AND REACTIVITY OF THE ALPHA-KETOL ENT-3BETA-HYDROXYBEYER-15-ENE-2,12-DIONE, ITS CORRESPONDING DIOSPHENOL, AND SYNTHESIS OF THE ISOMERIC ALPHA-KETOL ACETATES

被引：10

作者：

PIACENZA, LPL

PEGEL, KH

PHILLIPS, L

WAIGHT, ES

机构：

[1] UNIV NATAL,DEPT CHEM,DURBAN,SOUTH AFRICA

[2] UNIV LONDON IMPERIAL COLL SCI & TECHNOL,DEPT CHEM,LONDON SW7 2AY,ENGLAND

[3] UNIV DURBAN WESTVILLE,DEPT CHEM,DURBAN,SOUTH AFRICA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 04期

关键词：

D O I：

10.1039/p19790001004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The major diterpenoid constituents of the heartwood of the Euphorbiaceae Androstachys johnsonii Prain are ent-3β-hydroxybeyer-15-ene-2,12-dione and the corresponding 2,3,12-trione. The four isomeric 2,3-α-ketol acetates were prepared by new and established methods and the chemistry of these α-ketols was investigated. A condensation reaction with ethylene glycol led to the useful ring A 2,3-ethylenedioxy blocking group. The 12-equatorial alcohol was eliminated yielding the new tetracyclic skeleton ent-14(13 → 12)abeo-beyerane. The ent-3β-hydroxy-2-ketone function was epimerised to the ent-3α-acetoxy-2-ketone function via the derived pyrrolidine enamine.

引用

页码：1004 / 1012

页数：9

共 34 条

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