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KMID : 1059519860300010109
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Journal of the Korean Chemical Society
1986 Volume.30 No. 1 p.109 ~ p.117
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Total Synthesis of 7,9-Dideoxydaunomycinone, Aglycone of Antitumor Antibiotic Daunorubicin (Ⅰ)
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Cho In-Ho
Rhee Richard P.
Rho Young-S.
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Abstract
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7,9-Dideoxydaunomycinone (32), a late-stage precursor of the aglycone of antitumor antibiotic daunorubicin(2a) was prepared from 3-methoxybenzoic acid(5). Thus, 3-methoxybenzoic acid was converted to 4-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone(11), which furnished trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rhee. The trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rbee. The trimethoxynaphtboate 16 was then transformed into phenylsulfonylnaphthofuranone 22, which was used to make anthracenoate 24 via Michael type reaction with 7-(ethylenedioxy)-2-octenoate(23). Conversion of anthracenoate 24 to tetracyclic product 28, followed by subsequent deprotection of the methyl groups in ring-B and C furnished 7, 9-Dideoxydaunomycinone(32).
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KEYWORD
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