An Approach to Pseudomonic Acids from D-Xylose

Article abstract of DOI:10.1021/jo00242a017

The four contiguous chiral centers present in pseudomonic acid C are constructed in an efficient way from D-xylose.The key steps involve a highly selective intermolecular radical reaction between benzyl 4-bromo-4-deoxy-2,3-di-O-benzoyl-β-L-lyxopyranoside (9) and phenyl vinyl sulfone for incorporating the lower appendage and a stereoselective intramolecular Michael addition to achieve the correct stereochemistry at the anomeric site.