Total asymmetric synthesis of Seco-acids of 9,12 anhydroerythronolide aglycons

Article abstract of DOI:10.1016/S0040-4039(98)00691-1

The Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'S)- camphanate was converted into (2R,3R,4S,5S,6R,7R)-3,6-epoxy-4,5- isopropylidenedioxy-2,4,6-trimethyl-7-[(tert-butyl)-dimethylsilylloxy]non-I- yl phenyl sulfoxides (6), the condensation of which with (3R,4S,5R,6S)-7- benzyloxy-3,5-isopropylidenedioxy-4,6-dimethylheptan-2-one (7) led to the partially-protected seco-acid of the 9,12-anhydroerythronolide aglycon (5).