title: Stereochemical Complexity in Oxocarbenium-Ion-Initiated Cascade Annulations for the Synthesis of the ABCD Core of Mattogrossine.
abstract: Mattogrossine is an indole alkaloid isolated from Strychnos mattogrossensis that contains an unusual tetrahydrofuran ring with a concomitant hemiacetal in its structure. While tetrahydrofuran intermediates have been used in the synthesis of other strychnos alkaloids, no investigations have been performed into the synthesis of alkaloids containing this structure. We have developed an oxocarbenium-ion-initiated cascade annulation that provides us access to the ABCD ring structure of mattogrossine.
authors.affiliation: Department of Chemistry, Emory University , Atlanta, Georgia 30322, United States.
authors.forename: Aidi
authors.initials: A
authors.lastname: Kong
authors.affiliation: Department of Chemistry, Emory University , Atlanta, Georgia 30322, United States.
authors.forename: Eric S
authors.initials: ES
authors.lastname: Andreansky
authors.affiliation: Department of Chemistry, Emory University , Atlanta, Georgia 30322, United States.
authors.forename: Simon B
authors.identifier: 0000-0002-4100-8610
authors.initials: SB
authors.lastname: Blakey
mesh_terms: D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C030011:carbene; D008697:Methane