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

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...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (1), p.209-211
Main Authors: McGrath, Nicholas A, Binner, Joshua R, Markopoulos, Georgios, Brichacek, Matthew, Njardarson, Jon T
Format: Article
Language:English
Subjects:
Asymmetry
Biological Products - chemical synthesis
Biological Products - chemistry
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Computer Simulation
Cyclization
Free Radicals - chemistry
Molecular Structure
Natural products
Oxidation-Reduction
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemical synthesis
Phloroglucinol - chemistry
Radicals
Stereoisomerism
Strength
Terpenes - chemical synthesis
Terpenes - chemistry
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c0cc01419b