title: An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.
abstract: This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80532-1872, USA.
authors.forename: Ke
authors.initials: K
authors.lastname: Kong
authors.forename: John A
authors.initials: JA
authors.lastname: Enquist
authors.forename: Monica E
authors.initials: ME
authors.lastname: McCallum
authors.forename: Genessa M
authors.initials: GM
authors.lastname: Smith
authors.forename: Takanori
authors.initials: T
authors.lastname: Matsumaru
authors.forename: Elnaz
authors.initials: E
authors.lastname: Menhaji-Klotz
authors.forename: John L
authors.initials: JL
authors.lastname: Wood
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D009930:Organic Chemicals; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D026121:Indole Alkaloids; D009930:Organic Chemicals; C503673:citrinadin A