Gilvocarcin antibiotics

Intramolecular biaryl couplingA novel, concise route to the benzonaphtho-pyranone ring system (4) of the aglycones of the gilvocarcin antibiotics uses an... 

Morimoto, M., Okubo, S., Tomita, F., andMarumo, H. 1981. Gilvocarcins, new antitumor antibiotics. 3. Antitumor activity. J. Antibiot. (Tokyo) 34, 701-707. 

Farr, R N, Kwok, D I, Daves, G D Jr, 8-Ethenyl-l-hydroxy - 3-D-ribofuranosylbenzo[d]naphtho[l, 2-b ]pyran-6-one and 8-ethenyl-1 -hydroxy-4-(2 -deoxy-p-D-ribofuranosyl)benzo[d ] naphtho[ 1,2-b ]pyran-6-one. Synthetic C-glycosides related to the gilvocarcin, ravidomycin, and chrysomycin antibiotics, J. Org. Chem., 57, 2093-2100, 1992. 

A key step in the synthesis of Gilvocarcin M 713, an aryl C-glycoside antibiotic, is the regioselective cycloaddition of the aryne derived from 711 to 2-methoxyfuran, to give... 

Another new anti-tumour antibiotic, virenomycin A, has the branched-chain sugar 6-deoxy-3-C-methyl-D-gulopyranoside (37) -linked as a C-glycoside to the same aglycone present in gilvocarcin V and ravidomycin (see Vol.17,p.181,182). 

A total synthesis of both enantiomers of the C-glycoside antibiotic gilvocarcin M utilizes an 0-+C glycoside rearrangement. The natural enantiomer was thesized from D-fucose. The total synthesis of aryl C-glycoside antibiotics has been reviewed. 

An antibiotic (31) isolated from a Streptomyces sp. has been shown to be identical with toromycin and gilvocarcin V, (see Vol. 15, p. 192). On acid-catalysed isomerization, a mixture of C-o and 3-fucofuranosides and C-3-fucopyranoside was obtained, which... 

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