The total synthesis of AB3217-A, a novel anti-mite substance, via intermolecular etherification and intramolecular glycosylation

M. Nakata, T. Tamai, T. Kamio, M. Kinoshita, K. Tatsuta

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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-me thoxyphenyl)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-xylofu ranoside which was prepared from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, via an intermolecular etherification. 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 AH3217-A.

Original languageEnglish
Pages (from-to)3057-3066
Number of pages10
JournalBulletin of the Chemical Society of Japan
Volume67
Issue number11
DOIs
Publication statusPublished - 1994 Dec 1

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ASJC Scopus subject areas

  • Chemistry(all)

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