A synthetic approach to benanomicin A. 2. Synthesis of the substituted 5,6-dihydrobenzo[a]naphthacenequinone.
The key intermediate tri-substituted alpha-tetralone (8) has been synthesized, either via tandem Michael addition-Dieckmann condensation reaction between dienolate and methyl crotonate in a low yield or via Barton's radical decarboxylation of diester (9) without 4-dimethylaminopyridine in 75% yield, and applied to the synthesis of the substituted 5,6-dihydrobenzo[a]naphthacenequinone.
Nishizuka
T
T
Institute of Microbial Chemistry, M. C. R. F., Tokyo, Japan.
Hirosawa
S
S
Kondo
S
S
Ikeda
D
D
Takeuchi
T
T
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000095643:Pradimicins and Benanomicins
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; C056805:benanomicin A; D000095643:Pradimicins and Benanomicins