Organic letters

A practical synthesis of (±)-α-isosparteine from a tetraoxobispidine core

PR Blakemore, C Kilner, NR Norcross, PC Astles

Index: Blakemore, Paul R.; Kilner, Colin; Norcross, Neil R.; Astles, Peter C. Organic Letters, 2005 , vol. 7, # 21 p. 4721 - 4724

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Citation Number: 25

Abstract

The title alkaloid was synthesized in racemic form from 3, 7-diallyl-2, 4, 6, 8-tetraoxo-3, 7- diazabicyclo [3.3. 1] nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to α- isosparteine was conducted on a multigram scale and proceeded without recourse to ...