Pillaromycin-A: structural and synthetic studies related to the sugar moiety, pillarose

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Abstract
The photo-induced alkylation of enone 6 with ethylene glycol gave an adduct from which the α-D-threo (16) and α-D-erythro (17) modifications of structure 2 have been elaborated. It was thereby shown that 2 is not the structure of pillarose. Addition of vinyl magnesium bromide to the ketone 24b gave a slight excess of one allylic alcohol, 25, which upon treatment with osmium tetroxide and hydrogen peroxide gave directly the α,α′-ketodiol 3a. The epimer of the latter 33b was available via carboxymethylenation of ketone 24b, reduction of ester, and hydroxylation. Benzoylation of these epimers gave 3b and 33c respectively and it was concluded that the former, methyl 2,3,6-trideoxy-4-C-[oxo(benzoyloxymethyl)methyl]-α-D-threo-hexopyranoside, 3b, is the enantiomer of the "methyl 8-O-benzoyl pillaroside" obtained from the antibiotic pillaromycin A.

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