Total Synthesis of (±)-Phomactin G, a Platelet Activating Factor Antagonist from the Marine Fungus Phoma sp.

William Goldring, G. Pattenden

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

A total synthesis of phomactin G (3), which is a central intermediate in the biosynthesis of phomactin A (5) in Phoma sp. is described. The synthesis is based on a Cr(II)/Ni(II) macrocyclisation from the aldehyde vinyl iodide 9, leading to 16, followed by sequential conversion of 16 into the -epoxide 21 and the ketone 25 which, on deprotection, led to (±)-phomactin G. Phomactin G (3) shares an interesting structural homology with phomactin D (2), the most potent PAF-antagonist metabolite in Phoma sp. It is most likely converted into phomactin A (5), by initial allylic oxidation to the transient -alcohol phomactin structure 4, known as Sch 49028, followed by spontaneous pyran ring formation.
Original languageEnglish
Pages (from-to)466-473
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume2(4)
Issue number4
DOIs
Publication statusPublished - 21 Jan 2004

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

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