Abstract

Project Title: Progress Toward the Total Synthesis of Cryptocaryol A
Students: Erin Boedicker ’17 and Zhiyao Li ’17
Mentor: Dr. Mark Mitton-Fry

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.