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KMID : 1059519930370010141
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Journal of the Korean Chemical Society
1993 Volume.37 No. 1 p.141 ~ p.147
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Total Synthesis of 6-Deoxybisanhydrodaunomycinone Anticancer Antibiotics
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Cho In-Ho
Rho Young-Soy
Park Si-Ho
Ahn Koo-Hyeon
Sin Hong-Sig
Han Byoung-Ku
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Abstract
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A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with methyl vinyl ketone (19) to furnish 20.
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