Detailed in this communication is an efficient synthetic approach towards the guttiferone family of natural products. Oxidatively unraveling a para-quinone monoketal followed by consecutive 5-exo radical cyclizations provides the bicyclic core. An additional strength of this approach is a late stage asymmetric desymmetrization of an advanced symmetric intermediate.
The core structure (VI) of guttiferone terpenes such as (VII) is prepared via a diacetoxyiodobenzene--mediated oxidative dearomatization of phenol (II) and a subsequent radical cyclization of the resulting ketal as key steps. -(MCGRATH, N. A.; BINNER, J. R.; MARKOPOULOS, G.; BRICHACEK, M.; NJARDARSON*, J. T.; Chem. Commun. (Cambridge) 47 (2011) 1, 209-211, http://dx.
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