A solid-phase approach to the phallotoxins: total synthesis of [Ala7]-phalloidin |
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Authors: | Anderson Marc O Shelat Anang A Guy R Kiplin |
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Institution: | Department of Pharmaceutical Chemistry, University of California at San Francisco, California 94143-2280, USA. |
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Abstract: | Herein we report a solid-phase synthetic approach to Ala7]-phalloidin (1). Prior syntheses of phallotoxins were carried out using solution-phase routes that required large scale and preclude library production. The route presented here consists of solution-phase preparation of key orthogonally protected amino acid building blocks, followed by a solid-phase peptide synthesis sequence, featuring two resin-bound macro-cyclization reactions. The final product mixture was composed of two atropisomeric compounds, one designated "natural" (1) and the other designated "non-natural" (1'). The structures of these species were modeled using restrained energy minimization with NMR-derived restraints. |
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