Confirmation of the absolute configuration at C45 of amphidinol 3

Yoshiyuki Manabe, Makoto Ebine, Nobuaki Matsumori, Michio Murata, Tohru Oishi

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Amphidinol 3 (AM3), a membrane-active agent isolated from the dinoflagellate Amphidinium klebsii, consists of a long carbon chain containing 25 stereogenic centers. Although the absolute configuration of AM3 was determined by extensive NMR analysis and degradation of the natural product, the partial structure corresponding to the tetrahydropyran ring system was found to be antipodal to that of karlotoxin 2, a structurally related compound recently isolated from the dinoflagellate Karlodinium veneficum. By extensive degradation of the natural product and conversion of the resulting alcohol to an MTPA ester, the absolute configuration at C45 of AM3 was confirmed to be R, supporting the originally proposed structure.

Original languageEnglish
Pages (from-to)2003-2006
Number of pages4
JournalJournal of Natural Products
Volume75
Issue number11
DOIs
Publication statusPublished - Nov 26 2012

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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