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Note | Special issue | Vol 70, No. 1, 2006, pp.609-617
Published online, 17th October, 2006
DOI: 10.3987/COM-06-S(W)45
A Stereocontrolled Synthesis of (±)-β-Isosparteine

Paul R. Blakemore,* Neil R. Norcross, Stuart L. Warriner, and Peter C. Astles

*Department of Chemistry, Oregon State University, Gilbert Hall 153, Corvallis, Oregon 97331, U.S.A.

Abstract

A versatile tetraoxobispidine synthon, 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (1), was converted to the title alkaloid via a synthetic sequence incorporating: imide reduction, Sakurai allylation, and ring-closing olefin metathesis reactions.