Progress Toward the Total Synthesis of Cryptocaryol A

Schimmel/Conrades Science Center Atrium

Cryptocaryol A is a stereochemically complex natural product with potential anticancer properties. A convergent, stereoselective, and concise (11-step) total synthesis has been devised, and progress toward the completion of this synthesis is reported. The stereocenters have been installed using a combination of asymmetric allylation using Leighton's reagent and internal stereorelay. Key steps include an asymmetric bis-allylation, terminus differentiation via ring-closing metathesis, a chemoselective alkene oxidation using ozone, and a boron aldol reaction with 1,5-anti stereoinduction.