Asymmetric total synthesis of rollicosin.
[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.
Quinn
Kevin J
KJ
Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610-2395, USA. kquinn@holycross.edu
Isaacs
André K
AK
DeChristopher
Brian A
BA
Szklarz
Stephanie C
SC
Arvary
Rebecca A
RA
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
D005663:Furans; D007783:Lactones; C475244:rollicosin