Rapid, high-yield, solid-phase synthesis of the antitumor antibiotic sansalvamide a using a side-chain-tethered phenylalanine building block

Younghee Lee, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticle

49 Scopus citations

Abstract

(matrix presented) A 10-step solid-phase synthesis of the cytotoxic depsipeptide sansalvamide A (1) has been accomplished in an overall yield of 67% with >95% purity employing polymer-bound phenylalanine building block 2. Both the N- and C-termini of 2 are extended followed by on-resin head-to-tail macrocyclization of the linear peptide in a high yield. This should be a general stategy for the synthesis of diverse libraries of cyclic peptides and depsipeptides that contain exclusively phenylalanine and other hydrophobic side chains.

Original languageEnglish (US)
Pages (from-to)3743-3746
Number of pages4
JournalOrganic Letters
Volume2
Issue number23
DOIs
StatePublished - Nov 16 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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