Journal of Organic Chemistry p. 4491 - 4493 (1989)
Update date:2022-08-04
Topics: Stereoselective synthesis
Winkler, Jeffrey D.
Lee, Chih-Shone
Rubo, Lauri
Muller, Cheryl L.
Squattrito, Philip J.
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.
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