TY - JOUR
T1 - A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A
AU - Novak, Alexander J.E.
AU - Grigglestone, Claire E.
AU - Trauner, Dirk
N1 - Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/10/2
Y1 - 2019/10/2
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.9b08892
DO - 10.1021/jacs.9b08892
M3 - Article
C2 - 31518120
AN - SCOPUS:85072849261
SN - 0002-7863
VL - 141
SP - 15515
EP - 15518
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 39
ER -