title: Synthesis of the Common Core Structure of the Stemofoline Alkaloids.
abstract: A novel synthetic route to the common core structural motif of the stemofoline alkaloids has been developed. The key transformations include (1) an intramolecular 1,3-dipolar cycloaddition reaction of a highly functionalized nitrone, (2) the subsequent formation of a caged structure via lithiated allylic sulfoxide, and (3) the concomitant sila-Pummerer reaction of α-silylalkenyl sulfoxide to prepare a thioester precursor. A series of stereochemistries on the highly caged core structure characteristic of the stemofoline alkaloids was successfully assembled.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Eiji
authors.initials: E
authors.lastname: Ideue
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya University , Furo-cho, Chikusa, Nagoya, Aichi 464-8601, Japan.
authors.forename: Jun
authors.initials: J
authors.lastname: Shimokawa
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya University , Furo-cho, Chikusa, Nagoya, Aichi 464-8601, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D009589:Nitrogen Oxides; C015388:nitrones; C430220:stemofoline