Hydroxycyclopentanone Derivativesfromd-Mannose via Ring Closing Metathesis:An Improved Synthesis of a Key Intermediate of Tricyclo-DNA

Abstract

A large scale, 10 step synthesis of cyclopentanone 1 , starting from the chiral pool compound D-mannose, is described. The synthesis proceeds via a ring closing metathesis reaction as the key step in an overall yield of 23%. Cyclopentanone 1 is a central intermediate for the synthesis of tricyclo-DNA