Novel Synthesis of 3,5,5‐Trimethyl‐4‐(2‐butenylidene)‐cyclohex‐2‐en‐1‐one, a Major Constituent of <i>Burley</i> Tobacco Flavour

Abstract

Abstract The acetylenic diol 2 , prepared by reaction of but‐3‐yn‐2‐ol dianion with 2,6,6‐trimethyl‐4,4‐ethylenedioxy‐cyclohex‐2‐en‐1‐one ( 1 ), afforded 3,5,5‐trimethyl‐4‐(2‐butenylidene)‐cyclohex‐2‐en‐1‐one ( 4 ), a major constituent of Burley tobacco flavour, upon LiAlH 4 reduction and hydrolysis. Vomifoliol ( 5 ) and blumenol C ( 6 ) were major by‐products in this reaction.