SYNTHESIS OF VICINAL STEREOGENIC TERTIARY AND QUATERNARY CENTERS USING CHIRAL BICYCLIC LACTAMS AND DIASTEREOSELECTIVE PROTONATION - ASYMMETRIC-SYNTHESIS OF (+)-LAURENE

被引:21
作者
SCHWARZ, JB [1 ]
MEYERS, AI [1 ]
机构
[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
关键词
D O I
10.1021/jo00125a042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chiral bicyclic lactam 5, previously reported in the synthesis of(-)-alpha-cuparenone, was used to construct the more complex title compound 2. A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess. Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.
引用
收藏
页码:6511 / 6514
页数:4
相关论文
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