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Novel Syntheses of Isomers of Damascenone from Ethyl 2,6,6-Trimethyl-4-oxo-2-cyclohexene-1-carboxylate
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  • Novel Syntheses of Isomers of Damascenone from Ethyl 2,6,6-Trimethyl-4-oxo-2-cyclohexene-1-carboxylate
  • Novel Syntheses of Isomers of Damascenone from Ethyl 2,6,6-Trimethyl-4-oxo-2-cyclohexene-1-carboxylate
저자명
Lee. Woo-Young,Jang. Se-Young,Lee. Jun-Gu,Chae. Woo-Ki
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1991년|12권 1호|pp.31-35 (5 pages)
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대한화학회
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정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

Three isomers of damascenone, odorous terpenic ketones, have been synthesized conveniently from a same starting material, ethyl 2,6,6-trimethyl-4-oxo-2-cyclohexene-1-carboxylate(1), which was easily available by the acid-catalyzed condensation of mesityl oxide or acetone with ethyl acetoacetate. ${alpha}$-Damascenone(7) was prepared by converting the enone ester 1 into the corresponding tosylhydrazone(4), followed by treating with 4 molar equiv of allyllithium. ${eta}$-Damascenone(12) was synthesized by chemoselective reduction of 1 with sodium borohydride/cerium chloride to give corresponding allylic alcohol 8, conversion of 8 into acetate 9, and thermal decomposition of 9 with DBU to afford ethyl ${eta}$-safranate(10), followed by reaction with an excess amount of allyllithium. ${gamma}$-Damascenone(15) was obtained by dehydration of 8 with boric acid to furnish ${gamma}$-safranate(13), followed by treatment with 2 molar equiv of allyllithium.