Tetrahedron: Asymmetry

Synthesis of enantiopure (2R)-configured muscarine alkaloids via selective alkoxyl radical ring-closure reactions

J Hartung, R Kneuer

Index: Hartung, Jens; Kneuer, Rainer Tetrahedron Asymmetry, 2003 , vol. 14, # 19 p. 3019 - 3031

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Citation Number: 23

Abstract

A new synthesis of (−)-muscarine,(+)-allo-muscarine,(−)-epi-muscarine, and (−)-epiallo- muscarine has been devised which utilizes selective alkoxyl radical cyclizations for constructing tri-substituted tetrahydrofuran units. Photolysis of (2R, 3S)-N-(3-benzoyloxy-5- hexen-2-oxy)-4-methylthiazole-2 (3H) thione in the presence of BrCCl3 provided (2R, 3S, 5S)-3-benzoyloxy-5-bromomethyl-2-methyltetrahydrofuran as the major product and the ...