title: Asymmetric first total syntheses and assignment of absolute configuration of oxazinin-5, oxazinin-6 and preoxazinin-7.
abstract: Asymmetric first total syntheses of the unprecedented toxins oxazinin-5, oxazinin-6 and preoxazinin-7 have been achieved from a common key intermediate 18, derived from a regiocontrolled Sharpless asymmetric aminohydroxylation and oxa-Michael reaction, which in addition to confirming the structure also established the absolute configuration of the natural products. On the way an expeditious synthesis of a metabolite bursatellin was completed in 8 steps.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune, 411 008, India.
authors.forename: Dattatraya H
authors.initials: DH
authors.lastname: Dethe
authors.forename: Alok
authors.initials: A
authors.lastname: Ranjan
authors.forename: Vijendra H
authors.initials: VH
authors.lastname: Pardeshi
mesh_terms: D008968:Molecular Conformation; D009025:Morpholines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D009025:Morpholines; C569124:oxazinin-5; C569123:oxazinin-6; C569125:preoxazinin-7