Cis-stereoselective SmI2-promoted reductive coupling of keto-nitrones: first synthesis of 1-epitrehazolamine.

Géraldine Masson, Christian Philouze, Sandrine Py

LEDSS, UMR 5616 CNRS-Universite Joseph Fourier, BP 53, 38041 Grenoble, France.

Organic & biomolecular chemistry 2005 Jun 7

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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.

Citation

Géraldine Masson, Christian Philouze, Sandrine Py. Cis-stereoselective SmI2-promoted reductive coupling of keto-nitrones: first synthesis of 1-epitrehazolamine. Organic & biomolecular chemistry. 2005 Jun 7;3(11):2067-9