Construction of AB-Ring System of Taxane Framework by A-Ring Annulation Strategy: Synthesis of 1-Hydroxy-8,11,11-trimethylbicyclo-(5.3.1)undec-7-en-9-one by Way of Intramolecular Aldol Cyclization to Form the C1-C10 Bond.

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  • Construction of AB-Ring System of Taxane Framework by A-Ring Annulation Strategy:Synthesis of 1-Hydroxy-8,11,11-trimethylbicyclo〔5.3.1〕undec-7-en-9-one by Way of Intramolecular Aldol Cyclization to Form the C1-C10 Bond
  • Construction of AB-Ring System of Taxan

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Abstract

Construction of the AB-ring system of the taxane framework via an A-ring annulation strategy was demonstrated by base-mediated intramolecular aldol reaction of (Z)-2, 2-dimethyl-3-(1-methyl-2-oxopropylidene)cyclooctanone, affording the title compound, 1-hydroxy-8, 11, 11-trimethylbicyclo[5.3.1]undec-7-en-9-one. A cyclization precursor, the tetra-substituted (Z)-alkene, was prepared from the corresponding cyclooctanone derivative, 3-[(α, α-dimethylbenzyl)dimethylsiloxy]-2, 2-dimethylcyclooctanone via a bicyclic α, β-unsaturated lactone intermediate.

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