Reduction of 5-hydroxymethylene-cis-caran-4-one with complex hydrides

Abstract

Reduction of 5-hydroxymethylene-cis-caran-4-one (I) with lithium aluminium hydride gave 5-methylene-cis-caran-cis-and -trans-4-ols [(III) and (IV)] as main products, and small quantities of cis-5-methyl-cis-caran-4-one (II) and 5-hydroxymethyl-cis-car-4-ene (V), whereas reduction with sodium borohydride gave mainly 5-hydroxymethylcaran-4-ol (VI) with a lesser quantity of compounds (II)–(V). The mechanisms of these reactions are discussed.