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A regiospecific total synthesis of (±)-daunomycinone

✍ Scribed by Andrew S. Kende; James Rizzi; Jed Riemer

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
201 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

The pioneering work of Wong et al in 1971-73' was the first of a growing series of investigations toward the efficient laboratory synthesis of clinically useful anthracycline antibiotics. Although several total syntheses of (*)-daunomycinone (IIIa) and adriamycinone (IIIb) have been reported,' only recently have regiospecific syntheses of these molecules been achieved.3 In 1976 we described the conversion of our red tetracycllc ketone II to (+)-daunomycinone in approximately 10% yield.4 However, our three step preparation of ketone II from 1,4,5-trimethoxyanthraqulnone (I) by a Diels-Alder route was nonregiospecific, generating an equal amount of the corresponding C-8 ketone which had to be tediously separated from II. We now report a strategy which leads uniquely to isomer II, thereby comprising a regiospecific total synthesis of (*I-daunomycinone and its congeners.

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