Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers

Alan R. Healy, Francesco Vinale, Matteo Lorito, Nicholas J. Westwood

Research output: Contribution to journalArticlepeer-review

Abstract

The bioactive natural product harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of harzianic acid.

Original languageEnglish (US)
Pages (from-to)692-695
Number of pages4
JournalOrganic Letters
Volume17
Issue number3
DOIs
StatePublished - Feb 6 2015

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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