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Efficient and practical asymmetric synthesis of the taxol C-13 side chain and its analogs via chiral 3-hydroxy-4-aryl-beta-lactams

The lithium chiral ester enolate-imine cyclocondensation strategy is successfully applied to the asymmetric synthesis of the C-13 side chain of taxol, N-benzoyl-(2R, 3S)-3-phenylisoserine, and its analogs via 3-hydroxy-4-aryl-beta-lactams. This method provides the target molecules in 3 steps in good yield with virtually 100%e.e. The intermediate 3-hydroxy-beta-lactams can readily be coupled with a protected baccatin III after N-benzoylation and proper protection.

chiral 3-hydroxy-4-aryl-beta-lactams; taxol

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