Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane

Organic Letters
Romain CoffinierStéphane Quideau

Abstract

The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphenol using a novel C2-symmetrical chiral Salen-type bis(λ(5)-iodane).

References

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Citations

Feb 15, 2017·Chemistry : a European Journal·Nikita JainMarco A Ciufolini
Apr 14, 2017·Organic & Biomolecular Chemistry·Elsa Deruer, Sylvain Canesi
Mar 16, 2018·Organic & Biomolecular Chemistry·Andrew M Harned
May 5, 2016·Organic & Biomolecular Chemistry·Akira YoshimuraViktor V Zhdankin
Apr 28, 2018·Angewandte Chemie·Takuya HashimotoKeiji Maruoka
Aug 3, 2019·Organic & Biomolecular Chemistry·I F Dempsey HyattCyrus Mowdawalla
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Elsa DeruerSylvain Canesi

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