A divergent and stereoselective approach for the syntheses of (–)-zeylenol, (+)-6-O-benzoylzeylenol, (+)-uvarigranol E and (+)-uvarigranol F

Abstract

A common, divergent, efficient, and stereoselective approach to the total syntheses of four carbasugars, namely, (–)-zeylenol, (+)-6-O-benzoylzeylenol, (+)-uvarigranol E and (+)-uvarigranol F from d-mannose derived key intermediate 14 is described. This intermediate was synthesized using mixed aldol condensation, Grignard reaction and ring closing metathesis as key steps by our previous method in nine steps from d-mannose. From this intermediate, we achieved the syntheses of (+)-6-O-benzoylzeylenol, (+)-uvarigranol F in three steps, (+)-uvarigranol E in four steps and improved synthesis of (–)-zeylenol.