C-Aryl glycosides via tandem intramolecular benzyne-furan cycloadditions. Total synthesis of vineomycinone B2 methyl ester.
A triply convergent total synthesis of vineomycinone B2 methyl ester has been achieved by an approach with a longest linear sequence of 16 steps. The synthesis features the use of silicon tethers as disposable linkers to control the regiochemistry in two tandem Diels-Alder reactions of substituted benzynes and glycosyl furans to provide rapid access to the fully intact anthrarufin core of vineomycinone B2 methyl ester.
Chen
Chi-Li
CL
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
Sparks
Steven M
SM
Martin
Stephen F
SF
D000880:Anthraquinones / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D001555:Benzene Derivatives / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis*; D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005663:Furans / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D008745:Methylation; D008956:Models, Chemical; D013302:Streptomyces / Q000737:chemistry*
D000880:Anthraquinones; D000903:Antibiotics, Antineoplastic; D001555:Benzene Derivatives; D004952:Esters; D005663:Furans; D006027:Glycosides; C585971:vineomycinone B2 methyl ester; D005643:Fucose; C024277:vineomycin B2