Synthesis and complete stereochemical assignment of psymberin/irciniastatin A

Xin Jiang, Jorge Garcia-Fortanet, Jef K. De Brabander

Research output: Contribution to journalArticlepeer-review

88 Scopus citations

Abstract

We describe a concise and flexible synthetic avenue for the preparation of compounds with structures relevant to those proposed for the novel marine-derived differential cytotoxins psymberin and irciniastatin A. Our efforts led to their complete stereochemical assignment and the notion that psymberin and irciniastatin A are identical compounds. Our total synthesis features an interesting termini-differentiating lactolization of a dialdehyde obtained from a C2-symmetrical bis-olefin precursor, a mild platinum-catalyzed hydrolysis of an epimerizable nitrile, a novel protocol to prepare sensitive methyl imidates, and a one-pot conversion of these imidates to N-acyl aminals. Starting from fragments 5-7 (prepared in 7-8 steps each, 30-49% overall yield) the synthesis of psymberin/irciniastatin A was completed in an additional 9 steps and 30% yield (17 steps longest linear sequence, 8.9% overall).

Original languageEnglish (US)
Pages (from-to)11254-11255
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number32
DOIs
StatePublished - Aug 17 2005

ASJC Scopus subject areas

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

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