Total synthesis and structure-activity investigation of the marine natural product neopeltolide

Daniel W. Custar, Thomas P. Zabawa, John Hines, Craig M. Crews, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

83 Scopus citations

Abstract

The total synthesis and biological evaluation of neopeltolide and analogs are reported. The key bond-forming step utilizes a Lewis acid-catalyzed intramolecular macrocyclization that installs the tetrahydropyran ring and macrocycle simultaneously. Independent of each other, neither the macrolide nor the oxazole side chain substituents of neopeltolide can inhibit the growth of cancer cell lines. The biological data of the analogs indicate that alterations to either the ester side chain or the stereochemistry of the macrolide result in a loss of biological activity.

Original languageEnglish (US)
Pages (from-to)12406-12414
Number of pages9
JournalJournal of the American Chemical Society
Volume131
Issue number34
DOIs
StatePublished - Sep 2 2009

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

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