title: Formal total synthesis of (+)-trehazolin. Application of an asymmetric aldol-olefin metathesis approach to the synthesis of functionalized cyclopentenes.
abstract: An asymmetric synthesis of the aminocyclopentitol pseudosugar of trehazolin has been completed. The synthesis hinges on an asymmetric aldol-ring closing metathesis strategy to construct the five-membered ring with control of both the relative and absolute stereochemistry.
authors.affiliation: Venable and Kenan Laboratories of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA. crimmins@email.unc.edu
authors.forename: M T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: E A
authors.initials: EA
authors.lastname: Tabet
mesh_terms: D000475:Alkenes; D003517:Cyclopentanes / Q000138:chemical synthesis*; D004187:Disaccharides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared
chemical_list: D000475:Alkenes; D003517:Cyclopentanes; D004187:Disaccharides; D007202:Indicators and Reagents; C071816:trehazolin