Cis-stereoselective SmI2-promoted reductive coupling of keto-nitrones: first synthesis of 1-epitrehazolamine.
An expeditious synthesis of 1-epitrehazolamine is presented from readily available 2,3,4,6-tetra-O-benzyl-D-glucose. The key step involves a samarium diiodide-promoted reductive cyclization of a masked keto-nitrone to form a five-membered ring aminocyclitol. The excellent cis selectivity observed in this nitrone-ketone reductive coupling contrasts surprisingly with the trans selectivity of ketone-oxime reductive couplings.
Masson
Géraldine
G
LEDSS, UMR 5616 CNRS-Universite Joseph Fourier, BP 53, 38041 Grenoble, France.
Philouze
Christian
C
Py
Sandrine
S
D002244:Carbon / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis*; D009584:Nitrogen / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
C511419:1-epitrehazolamine; D003517:Cyclopentanes; D009589:Nitrogen Oxides; C015388:nitrones; D002244:Carbon; D009584:Nitrogen