Total Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage Sequence.
The total synthesis of (+)-cryptocaryol A was achieved in 20 steps from (R)-glycidol. The key steps were a Prins cyclization/reductive cleavage sequence to construct the C5-C11 polyol fragment, a diastereoselective aldol reaction to control the stereogenic center at C13, and a stereocontrolled reduction to introduce the stereogenic center at C15.
Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI) - UMR 8231 - ESPCI ParisTech/CNRS, PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Elodie
E
Brun
Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI) - UMR 8231 - ESPCI ParisTech/CNRS, PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Véronique
V
Bellosta
Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI) - UMR 8231 - ESPCI ParisTech/CNRS, PSL Research University , 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Janine
J
Cossy