A diversity-oriented synthetic approach to bengamides

A new approach to the bengamides, a new class of antitumor natural products of marine origin, is reported from epoxyamides, prepared by reaction of aldehydes with sulfur ylides. The synthetic strategy has been designed for the delivery of a wide array of analogues. Thus, the terminal alkyl substituent is introduced by a cross olefin metathesis from the corresponding terminal olefin. The combination of cross olefin metathesis, introduction of different nucleophiles by the oxirane ring opening and the introduction of different amines via amide bond formation, can produce a wide array of bengamides analogues.