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Synthesis 1992; 1992(12): 1248-1254
DOI: 10.1055/s-1992-26351
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Total Synthesis of the Biphenomycins; V.1 Synthesis of Biphenomycin A

Ulrich Schmidt* , Volker Leitenberger, Helmut Griesser, Johannes Schmidt, Regina Meyer
  • *Institut für Organische Chemie und Isotopenforschung der Universität Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, Germany
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Publication Date:
29 April 2002 (online)

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The total synthesis of biphenomycin A is described. Two of the five stereogenic centres were formed by enantioselective hydrogenation of the corresponding didehydroamino acids using the rhodium-DIPAMP catalyst and the two stereogenic centres of the α-amino-β-hydroxy unit were created by enantioselective hydrogenation using the ruthenium-BINAP catalyst or via a stereoselective aldol condensation, respectively. The biphenyl structural element was constructed by a palladium(0)-catalyzed coupling reaction. The 15-membered ansa ring was closed in 85 % yield by use of the appropriate, linear pentafluorophenyl ester in the two phase system chloroform/aqueous sodium hydrogen carbonate.