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

A.R. Healy, F. Vinale, M. Lorito, Nicholas James Westwood

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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
Pages (from-to)692-695
Number of pages4
JournalOrganic Letters
Volume17
Issue number3
Early online date28 Jan 2015
DOIs
Publication statusPublished - 6 Feb 2015

Fingerprint

Dive into the research topics of 'Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers'. Together they form a unique fingerprint.

Cite this