TOTAL SYNTHESIS OF THE MESO-TRITERPENE POLYETHER TEURILENE

被引：65

作者：

HASHIMOTO, M ^{[1
]}

HARIGAYA, H ^{[1
]}

YANAGIYA, M ^{[1
]}

SHIRAHAMA, H ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期

关键词：

D O I：

10.1021/jo00007a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

引用

页码：2299 / 2311

页数：13

共 34 条

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