关键词: 巨豆三烯酮, 保护基团, 消除, 香料

Abstract: Megastigmatrien-3-one is considered to be the most essential aroma constituent of tobacco and is widely applied in flavorings and perfumes as well as in the tobacco indus-try. This manuscript describes a new synthetic strategy for megastigmatrien-3-one synthe-sis using readily-available ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate as the starting material, which is then subjected to ketal protection and reduction with lithium aluminum hydride to produce the alcohol intermediate. The alcohol intermediate sub-sequently undergoes Swern oxidation, Grignard, and elimination reactions to afford the megastigmatrien-3-one with 40% total yield. This method features readily-available start-ing materials and mild reaction conditions, thereby exhibiting potential for further appli-cations.

Key words: megastigmatrien-3-one, protecting group, elimination, ?avor