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

Romain Coffinier (1) , Mourad El Assal (1) , Philippe A. Peixoto (1) , Cyril Bosset (1) , Karinne Miqueu (2) , Jean-Marc Sotiropoulos (2) , Laurent Pouységu (1) , Stéphane Quideau (1)

1 ISM - Institut des Sciences Moléculaires
2 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

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(λ5-iodane).

Domaines: Chimie

Romain Coffinier, Mourad El Assal, Philippe A. Peixoto, Cyril Bosset, Karinne Miqueu, et al.. Total Synthesis of (−)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane. Organic Letters, 2016, 18 (5), pp.1120--1123. ⟨10.1021/acs.orglett.6b00224⟩. ⟨hal-01494454⟩