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Title: Asymmetric total synthesis of rollicosin. Author: Quinn KJ, Isaacs AK, DeChristopher BA, Szklarz SC, Arvary RA. Journal: Org Lett; 2005 Mar 31; 7(7):1243-5. PubMed ID: 15787477. 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.[Abstract] [Full Text] [Related] [New Search]