Total synthesis of (+)-amphidinolide A. Structure elucidation and completion of the synthesis

Barry M. Trost, Paul E. Harrington, John D. Chisholm, Stephen T. Wrobleski

Research output: Contribution to journalArticle

52 Scopus citations

Abstract

The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of NMR chemical shift analysis and total synthesis. The 20-membered ring of amphidinolide A was formed by a ruthenium-catalyzed alkene-alkyne coupling to forge the C15-C16 bond. Using the reported structure 1 as a starting point, a number of diastereomers of amphidinolide A were prepared. Deviations of the chemical shift of key protons in each isomer relative to the natural material were used as a guide to determine the locations of the errors in the relative stereochemistry. The spectroscopic data for the synthetic and natural material are in excellent agreement.

Original languageEnglish (US)
Pages (from-to)13598-13610
Number of pages13
JournalJournal of the American Chemical Society
Volume127
Issue number39
DOIs
StatePublished - Oct 5 2005

ASJC Scopus subject areas

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

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