Diastereoselective synthesis of the polyol-containing side chain of the ent-bengamides

The synthesis of the non-natural antipode of the bengamide polyol-containing side chain has been achieved utilizing a diastereoselective oxygenated-enolate aldol reaction as the key step. A substrate-controlled reduction was used to complete the stereochemical array.     

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.