A Novel Prins Bicyclization Strategy for the Synthesis of Sugar Annulated Furopyran Scaffolds

作者：Srivastava Nikhil; Reddy P Puroshotham; Sridhar Balasubramanian; Reddy B V Subba^*

来源：Synlett, 2013, 24(10): 1263-1268.

DOI：10.1055/s-0033-1338708

• Prins bicyclization
• D-glucose
• sugar-annulated heterocycles
• metal triflate
• cooperative catalysis

A tandem Prins bicyclization of sugar-derived homoallylic diols with aldehydes has been accomplished using 10 mol% of In(OTf)(3) and 20 mol% of TsOH at ambient temperature to produce a novel series of sugar-annulated furopyran derivatives in good yields with high selectivity. This is the first report on Prins bicyclization of homoallylic diols derived from sugars. The cooperative catalysis between In(OTf)(3) and TsOH provides high conversions and enhanced reaction rates.

• 出版日期2013-6