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KMID : 1059519890330060644
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Journal of the Korean Chemical Society
1989 Volume.33 No. 6 p.644 ~ p.650
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Total Synthesis of 7-Deoxyaklavinone for Aklavin Anticancer Antibiotics
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Cho In-Ho
Chung Jin-Soon
Han Byoung-Ku
Yoo Dong-Jin
Lee Jun-Yong
Rho Young-Soy
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Abstract
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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).
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