title: Total synthesis of (-)-spinosyn A.
abstract: A convergent, highly stereoselective total synthesis of (-)-spinosyn A (1) is described. Key features of the synthesis include the transannular Diels-Alder reaction of macrocyclic pentaene 11 and the transannular Morita-Baylis-Hillman cyclization of 12 that generates tetracycle 26. The total synthesis of (-)-spinosyn A was completed by a sequence involving the highly beta-selective glycosidation reaction of 13 and glycosyl imidate 30.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
authors.forename: Dustin J
authors.initials: DJ
authors.lastname: Mergott
authors.forename: Scott A
authors.initials: SA
authors.lastname: Frank
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D002625:Chemistry, Organic / Q000379:methods; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007306:Insecticides; D018942:Macrolides; C114883:spinosyn A