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Efficient Biomimetic-Type Synthesis of the Benzo[a]naphthacenequinone Antibiotics G-2A and G-2N

✍ Scribed by Karsten Krohn; Sven Bernhard

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 279 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199911)1999:11<3099::aid-ejoc3099>3.0.co;2-2

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✦ Synopsis

Trioxo ester 15 was prepared by attachment of two vicinal C-16 regioselectively in one operation. Deprotection of 16 afforded the antibiotic G-2A (1) and decarboxylation of 1 4 and C-6 ketide side chains on the anthraquinone core (6b). Mild base treatment of 15 initiated successive aldol lead to G-2N (2). condensations to produce the benzo[a]naphthacenequinone

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