title: Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.
abstract: Oxidative allene amination provides rapid access to densely functionalized amine-containing stereotriads through highly reactive bicyclic methyleneaziridine intermediates. This strategy has been demonstrated as a viable approach for the construction of the densely functionalized aminocyclitol core of jogyamycin, a natural product with potent antiprotozoal activity. Importantly, the flexibility of oxidative allene amination will enable the syntheses of modified aminocyclitol analogues of the jogyamycin core.
authors.affiliation: Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
authors.forename: Nels C
authors.initials: NC
authors.lastname: Gerstner
authors.affiliation: Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Adams
authors.affiliation: Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
authors.forename: R David
authors.initials: RD
authors.lastname: Grigg
authors.affiliation: Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
authors.forename: Maik
authors.initials: M
authors.lastname: Tretbar
authors.affiliation: Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
authors.forename: Jared W
authors.initials: JW
authors.lastname: Rigoli
authors.affiliation: Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Schomaker
mesh_terms: D000466:Alkadienes / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010142:Pactamycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000466:Alkadienes; D000588:Amines; C000608051:jogyamycin; D010142:Pactamycin; C025947:propadiene