Total synthesis of the aglycone of the 8-methyl benzonaphthopyrone antibiotics, gilvocarcin M, virenomycin M, and albacarcin M

✍ Scribed by Michael E. Jung; Young H. Jung

• Book ID: 104220038
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 271 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)86100-6

✦ Synopsis

Attract: A short, convergent synthesis of the aglycone Sa of the S-methyl benxonaphthopytone antibiotics is described which utilizes as a hey step a Suzuki biaryl coupling. Recently a large group of antitumor antibiotics have been isolated from various strains of Streptotnyces,2-5 which all share the same general aglycone snucture -I-hydroxy-10,12dimethoxy-6Hbenxo[d]naphtho[l,2-b&ran-&one -with a substituent at C-8 (Methyl, yinyl, Ethyl) and differ mainly in the sugar moiety attached at C4. They include gilvocamin M la, V lb (also called toromycin), and E lc;2 virenomycin M and V (also called cbrysomycin A and B), 2ab;3 ravidomycin 3b;d and albacarcin M and V, 4ab.s.a Recent reports5~ that albacarcin M.and V 4ab both have good antitumor (P388) activity (V being about twice as potent as M) seems to contradict an