A SHORT FORMAL SYNTHESIS OF (-)-SERRICORNINE

被引:11
作者
PILLI, RA
DEANDRADE, CKZ
机构
[1] Universidade Estadual de Campinas, Instituto de Quimica, 13081-970 Campinas,SP
关键词
D O I
10.1080/00397919408013822
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short and efficient formal synthesis of serricornine (1), the sex pheromone of Lasioderma serricorne F., is described. The homochiral aldol 5 is straightforwardly converted to tosylate 9 to give homochiral lactone 2a (6 steps, 22% overall yield from oxazolidinone 4), a known precursor of (-)-1.
引用
收藏
页码:233 / 241
页数:9
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