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An efficient oxidative dearomatization-radical cyclization approach to symmetrically substituted bicyclic guttiferone natural products.

ABSTRACT: 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.

SUBMITTER: McGrath NA

PROVIDER: S-EPMC3107033 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

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An efficient oxidative dearomatization-radical cyclization approach to symmetrically substituted bicyclic guttiferone natural products.

McGrath Nicholas A NA Binner Joshua R JR Markopoulos Georgios G Brichacek Matthew M Njardarson Jon T JT

Chemical communications (Cambridge, England) 20100707 1

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. ...[more]

PMID: 20607196

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