Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Novel Glycosidation of 4-Demethoxyanthracyclinones by the Use of Trimethylsilyl Triflate. Syntheses of Optically Active 4-Demethoxydaunorubicin and 4-Demethoxyadriamycin
Yoshikazu KimuraMichiyo SuzukiTeruyo MatsumotoRumiko AbeShiro Terashima
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1986 Volume 59 Issue 2 Pages 423-431

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Abstract

Optically pure (+)-4-demethoxydaunorubicin has been prepared by a novel glycosidation reaction of (+)-4-demethoxydaunomycinone with (−)-3-N-trifluoroacetyl-1,4-bis(O-p-nitrobenzoyl)-L-daunosamine in the presence of trimethylsilyl triflate, followed by sequential O- and N-deprotection reactions. Total synthesis of optically pure (+)-4-demethoxyadriamycin has been also accomplished by two different synthetic schemes, starting from (+)-4-demethoxydaunorubicin or by way of (+)-3′-N-trifluoroacetyl-4-demethoxyadriamycin. (+)-4-Demethoxyadriamycin prepared by our hands was fully characterized by its spectral properties.

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