Affordable Access

Publisher Website

Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
19
Issue
16
Identifiers
DOI: 10.1016/j.tetasy.2008.08.002

Abstract

Abstract The enantiomerically pure tricyclic 9-oxabispidine (1 R,2 S,9 S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0 2,7]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and ( S)-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo-oriented side chain.

There are no comments yet on this publication. Be the first to share your thoughts.