Total Synthesis of the Biphenomycins; III.1 Synthesis of Biphenomycin B

Ulrich Schmidt; Regina Meyer; Volker Leitenberger; Helmut Griesser; Albrecht Lieberknecht

doi:10.1055/s-1992-26293

Synthesis 1992; 1992(10): 1025-1030
DOI: 10.1055/s-1992-26293

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Total Synthesis of the Biphenomycins; III¹.1 Synthesis of Biphenomycin B

Ulrich Schmidt^* , Regina Meyer, Volker Leitenberger, Helmut Griesser, Albrecht Lieberknecht

^*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 the cyclopeptide biphenomycin B (1b), a compound exhibiting a potent antibacterial activity against Gram-positive bacteria, is described. The non-proteinogenic amino acid (S,S)-diisotyrosine (2) was prepared by enantioselective hydrogenation of the corresponding didehydroamino acids. The 15-membered ansa ring was obtained in 85% yield within 5 minutes by ring closure of the appropriate linear pentafluorophenyl ester in the two phase system chloroform-aqueous sodium hydrogen carbonate without dilution.

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Total Synthesis of the Biphenomycins; III1.1 Synthesis of Biphenomycin B

Total Synthesis of the Biphenomycins; III¹.1 Synthesis of Biphenomycin B