A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A

Alexander J.E. Novak; Claire E. Grigglestone; Dirk Trauner

doi:10.1021/jacs.9b08892

A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A

Alexander J.E. Novak, Claire E. Grigglestone, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A short, biomimetic synthesis of the fungal metabolite preuisolactone A is described. Its key steps are a purpurogallin-type (5 + 2)-cycloaddition, followed by fragmentation, vinylogous aldol addition, oxidative lactonization, and a final benzilic acid rearrangement. Our work explains why preuisolactone A has been isolated as a racemate and suggests that the natural product is not a sesquiterpenoid but a phenolic polyketide.

Original language	English (US)
Pages (from-to)	15515-15518
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	141
Issue number	39
DOIs	https://doi.org/10.1021/jacs.9b08892
State	Published - Oct 2 2019

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.9b08892

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abstract = "A short, biomimetic synthesis of the fungal metabolite preuisolactone A is described. Its key steps are a purpurogallin-type (5 + 2)-cycloaddition, followed by fragmentation, vinylogous aldol addition, oxidative lactonization, and a final benzilic acid rearrangement. Our work explains why preuisolactone A has been isolated as a racemate and suggests that the natural product is not a sesquiterpenoid but a phenolic polyketide.",

author = "Novak, {Alexander J.E.} and Grigglestone, {Claire E.} and Dirk Trauner",

note = "Funding Information: We would like to thank New York University for a MacCracken Ph.D. fellowship (to A.J.E.N.) and the National Institutes of Health for financial support (Grant R01GM126228). This work was supported in part by the National Science Foundation through funding of the REU Site for Chemical Biology at New York University, under award number CHE-1659619. We would like to thank Michelle C. Neary and the Hunter College X-ray Facility for X-ray analysis and Dr. Bryan Matsuura and Dr. Nina Hartrampf for helpful discussions. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A

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ASJC Scopus subject areas

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