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

Nicholas A. McGrath; Joshua R. Binner; Georgios Markopoulos; Matthew Brichacek; Jon T. Njardarson

doi:10.1039/c0cc01419b

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

Nicholas A. McGrath, Joshua R. Binner, Georgios Markopoulos, Matthew Brichacek, Jon T. Njardarson

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

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.

Original language	English (US)
Pages (from-to)	209-211
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	1
DOIs	https://doi.org/10.1039/c0cc01419b
State	Published - Dec 6 2011
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c0cc01419b

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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.",

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AU - Brichacek, Matthew

AU - Njardarson, Jon T.

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AB - 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.

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

Abstract

ASJC Scopus subject areas

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