Reduction of Substituted 1-Methylene-1,2,3,4-tetrahydronaphthalene Derivatives

Abstract

The stereoselectivity of reduction of 4-substituted 1-methylene-1,2,3,4-tetrahydronaphthalenes has been investigated by using catalytic hydrogenation and lithium in ammonia solutions. Serrulatane derivatives underwent highly stereoselective catalytic reduction to yield cis products. Lithium/ammonia reduction was less selective but (3R)-7,8-dimethoxyserrulat-1(20)-en-3-ol showed good selectivity to yield predominantly the cis isomer.