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
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.
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页码:2299 / 2311
页数:13
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