title: Stereoselective synthesis of the butyrolactone and the oxazoline/furan fragment of leupyrrin A(1).
abstract: Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A1 are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.
authors.affiliation: University of Bonn, Kekule-Intitute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Debnar
authors.forename: Tongtong
authors.initials: T
authors.lastname: Wang
authors.forename: Dirk
authors.initials: D
authors.lastname: Menche
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D010080:Oxazoles; C481579:leupyrrin A1; D015107:4-Butyrolactone; C039281:furan