Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 25, Pages 4221-4224Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900595
Keywords
Total synthesis; Synthetic methods; Metathesis; Natural products; Azasugars
Categories
Funding
- CNRS and the Universite Joseph Fourier [UMR 5250, FR 2607]
- Research Ministry (MENRT)
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A highly efficient non-chiral-pool synthesis of (+)-1-deoxynojirimycin has been realized (24% overall yield, 11 steps, complete stereocontrol). A novel one-pot enol ether metathesis/hydroboration/oxidation sequence is used for the selective formation of the all-trans cyclic triol. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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