Journal of Organic Chemistry 2006-07-21

Asymmetric synthesis of enantioenriched (+)-elaeokanine A.

R Karl Dieter, Ningyi Chen

Index: J. Org. Chem. 71(15) , 5674-8, (2006)

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Abstract

The key transformation in the total synthesis of (+)-elaeokanine A was accomplished by asymmetric deprotonation of N-Boc pyrrolidine, followed by the reaction of the in situ generated enantioenriched stereogenic cuprate reagent with (E)-4-bromo-1-iodo-1-trimethylsilyl-1-butene with retention of configuration. N-Boc deprotection, followed by a one-pot olefin isomerization and intramolecular amine alkylation afforded a bicyclic vinyl bromide that was converted into (+)-elaeokanine A by sequential halogen metal exchange and reaction of the organolithium reagent with N-butanoylmorpholine.