ASYMMETRIC SYNTHESES OF SALVIA-MILTIORRHIZA ABIETANOID ORTHO-QUINONES - METHYL TANSHINONATE, TANSHINONE-IIB, TANSHINDIOL-B, AND 3-HYDROXYTANSHINONE

被引：39

作者：

HAIZA, M ^{[1
]}

LEE, J ^{[1
]}

SNYDER, JK ^{[1
]}

机构：

[1] BOSTON UNIV,DEPT CHEM,590 COMMONWEALTH AVE,BOSTON,MA 02215

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 17期

关键词：

D O I：

10.1021/jo00304a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reaction of 3-methyl-4,5-benzofurandione with vinylcyclohexene derivatives using either high-pressure or ultrasound promotion has led to the asymmetric synthesis of methyl tanshinonate, tanshinone IIB, tanshindiol B, and 3-hydroxytanshinone. The abietanoid diterpenes are active constituents of the Chinese traditional medicine, Dan Shen, prepared from the roots of Salvia miltiorrhiza Bunge. As a result, the absolute stereochemistry of these natural products has been assigned: (-)-(4S)-methyl tanshinonate, (-)-(4S)-tanshinone IIB, (-)-(3S,4R)-tanshindiol B, and (+)-(3S)-3-hydroxytanshinone. © 1990, American Chemical Society. All rights reserved.

引用

页码：5008 / 5013

页数：6

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