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Efficient Biomimetic‐Type Synthesis of the Benzo[ a ]naphthacenequinone Antibiotics G‐2A and G‐2N
Author(s) -
Krohn Karsten,
Bernhard Sven
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199911)1999:11<3099::aid-ejoc3099>3.0.co;2-2
Subject(s) - chemistry , aldol reaction , decarboxylation , vicinal , side chain , total synthesis , stereochemistry , antibiotics , anthraquinone , organic chemistry , catalysis , biochemistry , polymer
Trioxo ester 15 was prepared by attachment of two vicinal C‐4 and C‐6 ketide side chains on the anthraquinone core ( 6b ). Mild base treatment of 15 initiated successive aldol condensations to produce the benzo[ a ]naphthacenequinone 16 regioselectively in one operation. Deprotection of 16 afforded the antibiotic G‐2A ( 1 ) and decarboxylation of 1 lead to G‐2N ( 2 ).