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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 30, Number 5
JKCSEZ 30(5)
October 20, 1986 

Synthesis of Damascones and Related Flavoring Compound : β-Damascone

다마스콘 및 관련 향료물질의 합성 : 베타다마스콘
Woo Young Lee, Jung Mee Park, Ki Hong Nam, Se Young Jang, Oee Sook Park

이우영, 박정미, 남기홍, 장세영, 박외숙
방향을 지니는 천연물인 베타다마스콘(Ⅰ)을 2,2,6-트리메틸시클로헥산온(Ⅱ)으로부터 출발하여 합성하였다. 아세틸렌의 THF포화용액을 2차 부틸리튬으로 처리하여 얻은 모노아세틸화 음이온을 -78℃에서 (Ⅱ)와 반응시켜 에틴일하고, 이 때 생긴 에틴일카르비놀(Ⅲ)을 옥살산 또는 포름산과 함께 끓여서 이성질화시켜 일종의 아세틸시클로헥산(Ⅳ)을 얻었다. (Ⅳ)를 2차 부틸리튬으로 처리하여 생성되는 엔올화 음이온을 잘 건조시킨 아세트알데히드와 반응시켜서 생성되는 베타히드록시케톤(Ⅴ)을 파라톨루엔술폰산으로 탈수하여 트란스-2,2,6-트리메틸-1-크로톤일-1시글로 헥센, 즉 다마스콘(Ⅰ)을 합성하였다.

The synthesis of β-damascone (Ⅰ), an odoriferous natural product, was investigated from 2,2,6-trimethylcyclohexanone (Ⅱ); (Ⅱ) was ethynylated by the action of monoacetylide anion prepared from acetylene and sec-butyllithium at -78℃, to give an ethynylcarbinol(Ⅲ), which was isomerized to an acetylcyclohexene(Ⅳ) by refluxing in aqueous oxalic or formic acid. (Ⅳ) was treated with sec-butyllithium, the enolate was reacted with freshly dried acetaldehyde, and the resultant β-hydroxyketone (Ⅴ) was dehydrated by TsOH to β-damascone, trans-2,6,6-trimethyl-1-crotonyl-1-cyclohexene(Ⅰ).

483 - 487
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