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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 33, Number 6
JKCSEZ 33(6)
December 20, 1989

Title	Total Synthesis of 7-Deoxyaklavinone for Aklavin Anticancer Antibiotics 항암항생제 Aklavin의 7-Deoxyaklavinone 합성
Author	In Ho Cho, Jin Soon Chung, Byoung Ku Han, Dong Jin Yoo, Jun Yong Lee, Young Soy Rho 조인호, 정진순, 한병구, 유동진, 이준용, 노영소
Keywords
Abstract	Phthalide sulfone 2와 naphthalenone 6을 만들어서 Hauser-Rhee가 개발한 Michael addition의 새로운 고리 접합법으로 4개의 선형 고리화합물의 구조를 갖는 tetracyclic 화합물 11을 만들었다. 화합물 11의 ring A가 갖고 있는 중요한 이중결합을 이용해서 탄소수가 한 개 증가된 carbomethoxy 화합물 16으로 변형시키는 것은 Arndt-Eistert, Wolff rearrangement를 이용하였다. 그리고 나서 이들을 고리화 반응시킨 뒤 hydroxylation시켜서 최종 생성물인 (+)-7-Deoxyaklavinone(18)를 합성하였다. Syntheses of phthalide sulfone 2 and naphthalenone 6 followed by new ring annelation methodology of Michael addition using the sulfone anion developed by Hauser-Rhee, furnished linear tetracyclic ring system compound 11. The double bond existing in A-ring of 11 was used to convert to carbomethoxy compound 16, possessing one carbon atom more via Arndt-Eistert synthesis and Wolff rearrangement. Cyclization and hydroxylation of 16 completed the construction of (±)-7-Deoxyaklavinone (18).
Page	644 - 650
Full Text	PDF

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