Elsevier

Tetrahedron

Volume 44, Issue 13, 1988, Pages 4043-4060
Tetrahedron

Silicon-directed nazarov cyclizations VII: Linearly-fused tricyclics

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Abstract

A new modification of the silicon-directed Nazarov cyclization is described which involves the cyclization of divinyl ketones incorporating an allylsilane as the control unit. The cyclizations are extremely facile with FeCl3 or BF3·OEt2 as the Lewis acid. Four permutations of five- and six-membered ring substrates have been examined. In all cases the reactions are regio- and stereoslective. In the 6-5-6 (6ba) and 5-5-6 (6ba) systems the major product has the trans-anti configuration. The ability to incorporate a methyl substituent on the double bond and in the ring has been addressed.

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    NSF Presidential Young Investigator (1985–1990). Fellow of the Alfred P. Sloan Foundation (1985–1989).

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