Synthetic studies on the immunosuppressive agent FK-506: Enantioselective synthesis of a C22-C34 fragment

Article abstract of DOI:10.1016/S0040-4039(97)10532-9

The C28-C32 cyclohexyl group of the natural product, FK-506, was prepared enantioselectively from the iodolactone by replacement of iodide with retention of configuration. The C27-C28 trisubstituted olefin was introduced stereoselectively via a classical aldol/elimination sequence employing titanium enolate methodology. Elaboration of this chemistry has led to a synthesis of a C22-C34 fragment of the natural product.