Efficient biomimetic-type synthesis of the benzo [a]naphthacenequinone antibiotics G-2A and G-2N

Authors
Krohn, K Bernhard, S
Citation
K. Krohn et S. Bernhard, Efficient biomimetic-type synthesis of the benzo [a]naphthacenequinone antibiotics G-2A and G-2N, EUR J ORG C, (11), 1999, pp. 3099-3103
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
1999
Pages
3099 - 3103
Database
ISI
SICI code
1434-193X(199911):11<3099:EBSOTB>2.0.ZU;2-P
Abstract
Trioxo eater 15 was prepared by attachment of two vicinal C-4 and C-6 ketid e side chains on the anthraquinone core (6b). Mild base treatment of 15 ini tiated successive aldol condensations to produce the benzo[a]naphthacenequi none 16 regioselectively in one operation. Deprotection of 16 afforded the antibiotic G-2A (1) and decarboxylation of 1 lead to G-2N (2).