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Owen Callaghan, Christopher Lampard, Alan R. Kennedy and John A. Murphy
Abstract
The tetrathiafulvalene-induced ‘radical–polar crossover’ reaction has been applied to the total synthesis of the pentacyclic Aspidosperma alkaloid aspidospermidine.
References
Previous syntheses of aspidospermidine:
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Semi-empirical molecular modelling studies were performed at the AM1 level using Spartan 4.1, produced by Wavefunction Inc., Irvine, CA92715 .
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Enantiomerically pure aspidospermidine should be accessible by this route using a single enantiomer of 2-allylcylohex-2-en-1-ol, the ultimate source of this chiral centre (rather than the racemic compound used here). This compound has been prepared (ref. 19) in >96% ee and Mitsunobu reactions on cyclohex-2-enols have been found to proceed with clean inversion (ref. 20) of stereochemistry .
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TeXsan, Version 1.6, Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, Texas 77381, 1992 .
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