Total Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage Sequence

• DOI: 10.1021/acs.joc.5b01323
• Publication Date: 2015-08-04T21:37:58Z
• Authors: Elodie Brun; Véronique Bellosta; Janine Cossy
• Keywords: 01 natural sciences; 0104 chemical sciences; 3. Good health

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.