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The Total Synthesis of AB3217-A, a Novel Anti-mite Substance, via Intermolecular Etherification and Intramolecular Glycosylation

1994; Oxford University Press; Volume: 67; Issue: 11 Linguagem: Inglês

10.1246/bcsj.67.3057

1348-0634

Masaya Nakata, Tetsuro Tamai, Tadashi Kamio, Mitsuhiro Kinoshita, Kuniaki Tatsuta,

Chemical Synthesis and Analysis

Abstract The first total synthesis of AB3217-A has been achieved. The deacetylanisomycin unit, (3S,4S,5R)-3-benzyloxy-1-(benzyloxycarbonyl)-5-[(1R)-1-hydroxy-1-(4-methoxyphenyl)methyl]-4-(2-tetrahydropyranyloxy)pyrrolidine (18), was prepared from dimethyl l-tartrate by a stereoselective pyrrolidine-ring formation and a stereoselective reduction of phenyl ketone as the key steps. The lithium alkoxide of 18 was coupled with the d-xylofuranose unit, phenyl 2,3-di-O-benzyl-5-O-trifluoromethanesulfonyl-1-thio-α-d-xylofuranoside which was prepared from 1,2 : 5,6-di-O-isopropylidene-α-d-glucofuranose, via an intermolecular etherificaiton. The resulting coupling product was subjected to de-O-tetrahydropyranylation and an intramolecular glycosylation to afford 4,12,13-tribenzyl-6-(benzyloxycarbonyl)AB3217-A (30). Final deprotection of 30 furnished AB3217-A.