An enantiospecific synthesis of jiadifenolide.
A Robinson annulation, van Leusen homologation, and a desymmetrizing C-H oxidation enabled an enantiospecific synthesis of the neurotrophic natural product jiadifenolide. From a pulegone-derived building block, a key propellane intermediate was constructed through the use of simple reagents in a highly diastereoselective fashion. A short series of oxidations of this tricylic framework allowed progression to the natural product.
Frick Chemistry Laboratory, Department of Chemistry, Princeton University, Washington Road, Princeton, NJ 08544 (USA) http://www.princeton.edu/∼ejsgroup/
David A
DA
Siler
Jeffrey D
JD
Mighion
Erik J
EJ
Sorensen
D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D001688:Biological Products; D012717:Sesquiterpenes; D013729:Terpenes; C546282:jiadifenolide; D002244:Carbon; D006859:Hydrogen
CH activation; chiral pool; natural products; terpenoids; total synthesis