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Total synthesis of (±)-7-deoxydaunomycinone and (±)-7-deoxyisodaunomycinone

✍ Scribed by Robert D. Gleim; Steven Trenbeath; R.S.D. Mittal; Charles J. Sih

Publisher
Elsevier Science
Year
1976
Tongue
French
Weight
230 KB
Volume
17
Category
Article
ISSN
0040-4039

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✦ Synopsis

The anthracycline antibiotics, Daunorubicin', 1 and Adriamycin", 2 are established antineoplastic agents used for the clinical treatment of a broad spectrum of human cancers. The lack of an efficient biosynthetic process' coupled with their therapeutic importance have prompted the investigations of chemical synthesis to alleviate the scarcity of these drugs. 4,586 Recently, we described an effective route7 to the tetracyclic anthracyclinone ring system based on an efficient one-step cyclization of the tetrahydronaphthyl esters of 3-methoxy-phthalic acid, catalyzed by BF3-etherate.

We now report the successful adaptation of this approach to allow the synthesis of (_C)-7-deoxydaunomycinone, 16 and (+)-7-deoxyisodaunomycinone, 17.

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