Concise Total Syntheses of ∆¹²-Prostaglandin J Natural Products Using Stereoretentive Metathesis

Author: Li, Jiaming

Year: 2020

Degree: Dissertation (Ph.D.)

Advisors: Grubbs, Robert H.; Stoltz, Brian M.

Committee Members: Reisman, Sarah E.; Agapie, Theodor; Grubbs, Robert H.; Stoltz, Brian M.

Option: Chemistry

DOI: 10.7907/Q78K-7R18

Abstract

∆¹²-Prostaglandin J family is a type of secondary metabolite isolated in cell culture, and is recently discovered to have potent anticancer activity. Concise syntheses of four ∆¹²-prostaglandin J natural products (7–8 steps in the longest linear sequences) are developed, enabled by convergent stereoretentive cross-metathesis by Ru-based metathesis catalyst. Exceptional control of alkene geometry was achieved through stereoretention.

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