PENTACYCLIC TRITERPENE SYNTHESIS .5. SYNTHESIS OF OPTICALLY PURE RING AB PRECURSORS

被引：97

作者：

DUTCHER, JS ^{[1
]}

MACMILLAN, JG ^{[1
]}

HEATHCOCK, CH ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY, DEPT CHEM, BERKELEY, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1976年 / 41卷 / 16期

关键词：

D O I：

10.1021/jo00878a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bicyclic enone 5-methylene-1,1,4a.beta.-trimethyl-1,4,4a,5,8,8a.alpha.-hexahydronaphthalene-2,6(3H,7H)-dione 2-(2,2-aimethyl)trimethylene ketal (5), which is a precursor for rings A and B of the pentacyclic triterpenes, was synthesized in 10 steps from the enedione (.+-.)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione in 16% overall yield. Unsaturated keto alcohol (.+-.)-1,4a.beta.-dimethyl-5.beta.-hydroxy-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one was resolved into its enantiomers and absolute stereostructures assigned. The levorotatory enantiomer of 5 has the absolute configuration corresponding to that of the pentacyclic triterpenes.

引用

页码：2663 / 2669

页数：7

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