ASYMMETRIC DIELS-ALDER REACTIONS: EPC-SYNTHESIS OF A STABLE SARKOMYCIN PRECURSOR (CYCLOSARKOMYCIN)

Article abstract of DOI:10.1016/S0040-4039(01)93809-2

The first synthesis of enantiomerically pure cyclosarkomycin, a stable, crystaline precursor of the antitumor agent sarkomycin is reported.Key steps are an asymmetric Diels-Alder reaction of the (E)-3-bromoacrylate of (R)-pantolactone and introduction of oxygen funtionality via elimination/β-addition.The synthesis of cyclosarkomycin was accomplished in 9 steps in 17 percent overall yield.