Tetrahedron Letters

A short and efficient synthesis of unnatural (R)-nicotine

S Girard, RJ Robins, J Villiéras, J Lebreton

Index: Girard; Robins; Villieras; Lebreton Tetrahedron Letters, 2000 , vol. 41, # 48 p. 9245 - 9249

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Citation Number: 31

Abstract

A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration–cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51%(or in six steps with an overall yield of 65%).