Approach to the Total Synthesis of Chlorothricolide: Synthesis of "7-epi-Bottom Half" and Its Union with "Top Half" Systems

Article abstract of DOI:10.1021/jo00337a008

A synthesis of the "bottom half" of the antibiotic aglycon chlorothricolide (1) is described.Compound 1 was prepared in 13 steps from the readily available hydrobenzsuberone system 8; the process entails the stereoselective conjugate addition of <4-(benzyloxy)butyl>magnesium bromide to form the C ring.Union of the "top" and bottom" halves and decarbonylation of the derived aldehyde are explored.