The Journal of Organic Chemistry

Applications of intramolecular amidomercuration. 2. Synthesis of trans-5-hydroxy-2-propylpiperidine,(.+-.)-pseudoconhydrine

KE Harding, SR Burks

Index: Harding, Kenn E.; Burks, Stephen R. Journal of Organic Chemistry, 1984 , vol. 49, p. 40 - 44

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Citation Number: 82

Abstract

A method for the stereoselective conversion of 6-alkenyl carbamates into trans-2-alkyl-5- substituted-piperidines utilizing intramolecular amidomercuration as a key step has been developed. As a specific illustration of the method, a synthesis of one of the Hemlock alkaloids,(A)-pseudoconhydrine (trans-5-hydroxy-2-propylpiperidine, 1) was completed. The organomercurial 7a obtained from the intramolecular amidomercuration of 4-[(carbo- ...

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