Diastereoselective synthesis of chromans via silane reduction

ORGN 809

Kelin Li, kelinli@ku.edu and Jon A. Tunge, tunge@ku.edu. Department of Chemistry, University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Dr, Lawrence, KS 66045
Chroman derivatives exist in a wide range of bioactive natural products. The diastereoselective synthesis of chroman via silane reduction mediated by BF3∙Et2O leads to the effective synthesis of this type of privileged structure. A library of chromans was easily synthesized via the following three steps: intermolecular hydroarylation to form dihydrocoumarin, followed by nucleophilic attack of ArLi to give chromanol. And the stereochemical control reduction of chromanol to obtain the product. This methodology was also used for the synthesis of analogs of the natural product-Myristinins.