Tetrahedron

Copper mediated scalemic organolithium reagents in alkaloid syntheses

RK Dieter, N Chen, RT Watson

Index: Dieter, R. Karl; Chen, Ningyi; Watson, Rhett T. Tetrahedron, 2005 , vol. 61, # 13 p. 3221 - 3230

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Citation Number: 55

Abstract

Scalemic 2-pyrrolidinylcuprates generated via asymmetric deprotonation of N-Boc- pyrrolidine followed by treatment with THF soluble CuCN· 2LiCl react with ω-functionalized vinyl halides to afford 2-alkenyl-N-Boc-pyrrolidines. N-Boc deprotection and cyclization via intramolecular N-alkylation generates the pyrrolizidine or indolizidine skeletons. Subsequent functional group manipulation affords enantioenriched (+)-heliotridane,(+)- ...