Synthetic studies of carzinophilin. Part 1: Synthesis of 2-methylidene-1-azabicyclo[3.1.0]hexane systems related to carzinophilin
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چکیده
Synthesis of the model compounds of carzinophilin carrying 2-methylidene-1-aza-bicyclo[3.1.0]hexane systems was achieved. Formation of malonylidenes or N-acyl-glycinylidenepyrrolidines was carried out by utilizing Eschenmoser’s sulfide contraction or Herdeis’s condensation between the 2-methylthio-D-pyrrolone derivatives and ethyl nitroacetate, respectively. The 1-azabicyclo-[3.1.0]hexane systems were constructed by base-promoted aziridine formation. q 2003 Elsevier Science Ltd. All rights reserved.
منابع مشابه
Synthetic studies of carzinophilin. Part 2: Synthesis of 3,4- dibenzyloxy-2-methylidene-1-azabicyclo[3.1.0]hexane systems corresponding to the C1–C17 fragment of carzinophilin
A model compound bearing the C1–C17 fragment of carzinophilin was synthesized. The synthesis involved coupling reaction of a cyclic thioimidate with the 4H-oxazol-5-one derivative, ring-opening of the 4H-oxazol-5-one to furnish a dehydropeptide system, elaboration of the C1–C6 enolamide, and construction of the aziridine ring as key steps. q 2003 Elsevier Science Ltd. All rights reserved.
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تاریخ انتشار 2003