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KMID : 1059519920360060925
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Journal of the Korean Chemical Society
1992 Volume.36 No. 6 p.925 ~ p.932
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Total Synthesis of 9,10-Dideoxy-β-rhodomycinone
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Cho In-Ho
Rho Young-Soy
Sho Sang-Moon
Yoo Dong-Jin
Lee Jun-Yong
Han Byoung-Ku
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Abstract
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Total synthesis of 9,10-dideoxyrhodomycinone(30) which is the late-stage precursor of naturally occuring β-rhodomycinone(1) is described. After phthalide sulfone 4 was converted to naphthalide sulfone 12 by the several step. Michale addition of naphthalide sulfone 12 which was converted to an anion with 5-ethyl-1,3-cyclohexenone(21) gave a good yield of linearly condensed tetracyclic ketone compound 26. The keto group of 26 was reduced with sodium borohydride and protected by methyl group to afford compound 28. 9,10-Dideoxy-β-rhodomycinone(30) was synthesized from pentamethoxy tetracyclic compound 28 by oxidative demethylation and demethylation of 29.
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