Stereoselective Synthesis of the Tricyclic Skeleton of the Taxane Diterpenes: The First C-Silylation of a Ketone Enolate

Jeffrey D. Winkler, Chih Shone Lee, Lauri Rubo, Cheryl L. Muller, Philip J. Squattrito

Research output: Contribution to journalLetterpeer-review

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Abstract

The application of the intramolecular dioxenone photocycloaddition to the efficient synthesis of the tricyclic skeleton of the taxane diterpenes, with complete control of the relative stereochemical relationship between the two six-membered rings (A and C), is described. The first example of C-silylation of a ketone (cyclooctanone B-ring) enolate is reported, and the origins of this remarkable reactivity are discussed.

Original languageEnglish
Pages (from-to)4491-4493
Number of pages3
JournalJournal of Organic Chemistry
Volume54
Issue number19
DOIs
StatePublished - Sep 1 1989

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