AZA-[2,3]-WITTIG REARRANGEMENTS OF VINYLAZIRIDINES AS A NOVEL ENTRY TO INDOLIZIDINE ALKALOIDS - ENANTIOSELECTIVE TOTAL SYNTHESIS OF INDOLIZIDINE 209D

被引:69
作者
AHMAN, J [1 ]
SOMFAI, P [1 ]
机构
[1] LUND UNIV,LUND INST TECHNOL,CTR CHEM,S-22100 LUND,SWEDEN
关键词
D O I
10.1016/0040-4039(94)02236-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective total synthesis of indolizidine 209D (1) from epoxy alcohol 4 is described. The key step in the sequence involves an aza-[2,3]-Wiltig rearrangement of vinylaziridine 7 to yield the cis-2,6-disubstituted tetrahydropyridine 8 in 98% yield and as a single detectable diastereomer.
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页码:303 / 306
页数:4
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