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Synthesis 2000; 2000(7): 921-924
DOI: 10.1055/s-2000-6291
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A Carbometallation-Intramolecular Cycloaddition Strategy for the AB-Taxane Ring and an Enone Accelerated Cope Rearrangement to Bicyclo[2.2.2]octanones

Pat Forgione* , Peter D. Wilson, Glenn P. A. Yap, Alex G. Fallis
  • *Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada, K1N 6N5; Phone (613)5625732; Fax (613) 5625170; E-mail: afallis@science.uottawa.ca
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Publication Date:
31 December 2000 (online)

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The one pot transformation of the magnesium chelates, derived from alkynyl alcohols, into tetraene-diols for the construction of substituted bicyclo[5.3.1]undecenes is described. This sequence affords a direct route to the AB-taxane ring system via a Lewis acid catalyzed intramolecular Diels-Alder reaction. The cycloaddition gives a single diastereomer due to the preferential formation of the Et2AlCl chelate. This adduct undergoes a facile enone accelerated Cope rearrangement to generate a substituted bicyclo[2.2.2]octanone. This isomerization fails below 110 °C when the ketone is absent.

Cope - synthesis - Diels-Alder - taxoid - magnesium - propargyl