SYNTHESIS OF 4-DEOXY-β-RHODOMYCINONE VIA INCORPORATION OF A CHIRAL BUILDING BLOCK DERIVED FROM METHYL α-D-GLUCOPYRANOSIDE

Article abstract of DOI:10.1016/0008-6215(89)85069-4

Methyl 4,6-O-benzylidene-3-deoxy-2-C-ethyl-α-D-ribo-hexopyranoside was converted in six steps into (R)-3-benzyloxy-3-(trityloxymethyl)pentanal.This chiral building block was coupled to leucoquinizarin to afford 4-deoxy-γ-rhodomycinone, using two successive Marschalk reactions.Hydroxylation at C-7 gave 4-deoxy-β-rhodomycinone.