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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 38, Number 1
JKCSEZ 38(1)
February 20, 1994 

Study for Total Synthesis of Bruceantin Analogue(Ⅰ)

Bruceantin 유사체의 전합성에 대한 연구 (Ⅰ)
Jungho Ju, Jungjin Choi, Hongbum Kim

주정호, 최정진, 김홍범
Bruceantin유사체 전합성의 중요한 중간체인 ethyl (±)-8-oxo-10-oxa-l'H-spiro[1, 3]dioxolane-4,4'-tricyclo [ 1,6]dodec-6-ene-9-carboxylate (7)의 합성경로를 개발하였다. 시작물질로서 ethyl 2-cyclohexanonecarboxylate and methyl vinyl ketone을 사용하여, Robinson annulation, allylic oxidation등을 응용하였으며, regiospecific acylation and the formation of epoxy methano bridge 형성 반응 등이 연구되었다. Actalone (3)의 ketalization 반응에서 새로운 decarboethoxylation 반응을 발견하였으며, 이 반응을 이용하여 3차 알코올과 엔온을 가지고 있는 4,4a,5,6,7,8-Hexahydro-4a-hydroxy-2(3H)naphthalenone (14)를 합성하였다.

The synthetic pathway of ethyl (±)-8-oxo-10-oxa-l'H-spiro[1, 3]dioxolane-4,4'-tricyclo [ 1,6]dodec-6-ene-9-carboxylate (7), an important intermediate for the total synthesis of bruceantin analogue, was developed. Ethyl 2-cyclohexanonecarboxylate and methyl vinyl ketone were employed as starting materials. Robinson annulation, allylic oxidation, regiospecific acylation and the formation of epoxy methano bridge ring were studied. 4,4a,5,6,7,8-Hexahydro-4a-hydroxy-2(3H)naphthalenone (14) was synthesized utilizing the unusual decarboethoxylation reaction discovered during ketalization of octalone (3).

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