A diversity-oriented synthetic approach to bengamides |
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Authors: | Francisco Sarabia,Antonio Sá nchez-Ruiz |
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Affiliation: | Departamento de Bioquímica, Biología Molecular y Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071 Málaga, Spain |
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Abstract: | 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. |
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Keywords: | Bengamides LAF-389 Methionine aminopeptidase inhibitors Sulfur ylides Epoxyamides Cross metathesis Stereoselective synthesis |
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