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Grubbs' and Schrock's catalysts can be used in ring-closing metathesis reactions (RCM) to synthesize highly functionalized cyclooctenes that have the required stereochemistry for the C1, C2, and C8 centers of taxol. The unprecedented formation of a trans isomer in the case of the carbonate derivative (see scheme) indicates that RCM does not always proceed to complete thermodynamic equilibrium.
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Bourgeois et al. (2000) studied this question.
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