A solid-phase approach to the phallotoxins: Total synthesis of [Ala 7]-phalloidin

Marc O. Anderson, Anang A. Shelat, R. Kiplin Guy

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Herein we report a solid-phase synthetic approach to [Ala 7]-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.

Original languageEnglish
Pages (from-to)4578-4584
Number of pages7
JournalJournal of Organic Chemistry
Volume70
Issue number12
DOIs
StatePublished - Jun 12 2005

ASJC Scopus subject areas

  • Organic Chemistry

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