A synthetic approach to benanomicin A. 1. Synthesis of 5,6-dihydrobenzo[a]naphthacenequinone.
5,6-Dihydrobenzo[a]naphthacenequinone has been constructed by Diels-Alder reaction of an outer-ring diene with a naphthoquinone regioselectively. Similarly, the 14-hydroxy-5,6-dihydrobenzo[a]naphthacenequinone (13) has also been synthesized via the reaction of vinylketene acetal (11) with naphthoquinone.
Hirosawa
S
S
Institute of Microbial Chemistry, M. C. R. F., Tokyo, Japan.
Nishizuka
T
T
Kondo
S
S
Ikeda
D
D
Takeuchi
T
T
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D015394:Molecular Structure; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000737:chemistry; D009285:Naphthoquinones / Q000138:chemical synthesis*; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D000095643:Pradimicins and Benanomicins
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; D009279:Naphthacenes; D009285:Naphthoquinones; D011809:Quinones; C108554:5,6-dihydrobenzo(a)naphthacenequinone; C056805:benanomicin A; D000095643:Pradimicins and Benanomicins