Synthesis of necine bases from homoproline derivatives

Abstract
The α-ally homoproline ester 8, obtained by Claisen rearrangement of the allyl ester 7 or direct C-allylation of the homoproline methyl ester 9 has been converted into (–)-trachelanthamidine 4a and (–)-isoretronecanol 4b while allylation of the enolate derived from the lactone 13a followed by related transformations leads stereospecifically to turneforcidine 12.

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