Journal of Shanghai University(Natural Science Edition) ›› 2023, Vol. 29 ›› Issue (3): 562-.doi: 10.12066/j.issn.1007-2861.2360
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SHEN Jie1, LIANG Demin2, SHA Yunfei2, LI Jian1
Online:
Published:
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
CLC Number:
O 629.9
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(Natural Science Edition), 2023, 29(3): 562-.
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URL: https://www.journal.shu.edu.cn/EN/10.12066/j.issn.1007-2861.2360
https://www.journal.shu.edu.cn/EN/Y2023/V29/I3/562