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

doi:10.1021/ol503717r

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

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	692-695
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	3
DOIs	https://doi.org/10.1021/ol503717r
State	Published - Feb 6 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503717r

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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.",

author = "Healy, {Alan R.} and Francesco Vinale and Matteo Lorito and Westwood, {Nicholas J.}",

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AU - Lorito, Matteo

AU - Westwood, Nicholas J.

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AB - 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.

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

Abstract

ASJC Scopus subject areas

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