title: Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade.
abstract: Sweet to the core: Enantioselective formal total syntheses of the title compounds were accomplished in 24 steps from 2-deoxy-D-ribose. The synthesis features a novel cascade of reactions culminating in an intramolecular dipolar cycloaddition to form the tricyclic core of the stemofoline alkaloids from an acyclic diazo imine intermediate.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA.
authors.forename: Chao
authors.initials: C
authors.lastname: Fang
authors.forename: Charles S
authors.initials: CS
authors.lastname: Shanahan
authors.forename: Daniel H
authors.initials: DH
authors.lastname: Paull
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; C481859:didehydrostemofoline; C481860:isodidehydrostemofoline