An Intramolecular Diels-Alder Approach to the Synthesis of Chlorothricolide. Synthesis of (+/-)-24-O-Methylchlorothricolide

Article abstract of DOI:10.1021/jo00298a003

Cycloaddition of α-(acyloxy-γ-methylene-β-tetronate 16, obtained by condensation of three segments ((+/-)-11, 12, and 15), affords four diastereomeric macrolides 17a-d (1:2.8:1.9:0.9 ratio).The exo mode adduct 17a has been converted to (+/-)-24-O-methylchlorothricolide (19).