Total Synthesis of the Biphenomycins; V.1 Synthesis of Biphenomycin A

Ulrich Schmidt; Volker Leitenberger; Helmut Griesser; Johannes Schmidt; Regina Meyer

doi:10.1055/s-1992-26351

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

Abstract

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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.

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