title: Asymmetric total synthesis of rollicosin.
abstract: [structure: see text] The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation.
authors.affiliation: Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610-2395, USA. kquinn@holycross.edu
authors.forename: Kevin J
authors.initials: KJ
authors.lastname: Quinn
authors.forename: André K
authors.initials: AK
authors.lastname: Isaacs
authors.forename: Brian A
authors.initials: BA
authors.lastname: DeChristopher
authors.forename: Stephanie C
authors.initials: SC
authors.lastname: Szklarz
authors.forename: Rebecca A
authors.initials: RA
authors.lastname: Arvary
mesh_terms: D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D031045:Rollinia / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007783:Lactones; C475244:rollicosin