title: Total synthesis of jiadifenolide.
abstract: As a potent neurotrophic agent, the sesquiterpenoid jiadifenolide represents a valuable small-molecule lead for the potential therapeutic treatment of neurodegenerative diseases. A stereocontrolled total synthesis of this densely functionalized natural product is reported, central to which is an adventurous samarium-mediated cyclization reaction to establish the tricyclic core and the adjacent C5 and C6 quaternary stereocenters.
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK) http://www.paterson.ch.cam.ac.uk/. ip100@cam.ac.uk.
authors.forename: Ian
authors.initials: I
authors.lastname: Paterson
authors.forename: Mengyang
authors.initials: M
authors.lastname: Xuan
authors.forename: Stephen M
authors.initials: SM
authors.lastname: Dalby
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D012717:Sesquiterpenes; D014753:Vinyl Compounds; C546282:jiadifenolide
keywords: cyclization; neurological agents; samarium; terpenoids; total synthesis