Journal of Organic Chemistry p. 2607 - 2613 (1985)
Update date:2022-08-04
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Anzalone, Luigi
Hirsch, Jerry A.
Syntheses of the title compounds based on a Robinson annulation scheme utilizing tetrahydropyran-4-one are described.The 6-substituted system is elaborated by using Wittig methodology, while the 7-substituted ester is prepared via regioselective enolate formation.The regioselectivity of the latter is verified by preparation of a 5-isomer by reductive carboxylation of the original annulation product.Base-catalyzed equilibrations indicate a slightly preference for the equatorial position than in the 2-decalyl analogue, with entropy contributing little to theconformational free energies.
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