Formal total synthesis of (+)-trehazolin. Application of an asymmetric aldol-olefin metathesis approach to the synthesis of functionalized cyclopentenes.
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.
Crimmins
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Venable and Kenan Laboratories of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA. crimmins@email.unc.edu
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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
D000475:Alkenes; D003517:Cyclopentanes; D004187:Disaccharides; D007202:Indicators and Reagents; C071816:trehazolin