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.
SHEN Jie, LIANG Demin, SHA Yunfei, LI Jian
. Method for the synthesis of megastigmatrien-3-one using a novel starting material[J]. Journal of Shanghai University, 2023
, 29(3)
: 562
.
DOI: 10.12066/j.issn.1007-2861.2360