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 asymmetric desymmetrization of an advanced symmetric intermediate.
McGrath
Nicholas A
NA
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY, USA.
Binner
Joshua R
JR
Markopoulos
Georgios
G
Brichacek
Matthew
M
Njardarson
Jon T
JT
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003198:Computer Simulation; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D005609:Free Radicals; D013729:Terpenes; C522524:guttiferone G; D010696:Phloroglucinol