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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 14
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Original Articles

Syntisis of 4-Demethoxy-7, 11-dideoxydaunomycinone

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Pages 1219-1224 | Published online: 05 Dec 2006
 

Abstract

Our continued interest in the total synthesis of natural and unnatural antitumor anthracyclines1 especially the aglycones such as daunomycinone (1)2 and 4-demethoxydaunomycinone (2)3, 11-deoxydaunomycinone (3)4 and 4-demethoxy-11-deoxydaunomycinone (4)5 led us to probe methods of obtaining these products of absolute enantitomeric purity. Earlier it was demonstrated that the AB ring synthon 5 having a chiral centre on fusion with phthalic anhydride gave 4-demethoxy-7-deoxy-daunomycinone (6) with no loss of optical purity6 and the same was further transformed to 2 [7-(S)-9(S)].

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