Title

Progress Toward the Total Synthesis of Cryptocaryol A

Document Type

Article

Publication Date

4-20-2016

Abstract

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.

Faculty Mentor

Mark Mitton-Fry

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