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

Citation

Li, Jiaming (2020) Concise Total Syntheses of ∆¹²-Prostaglandin J Natural Products Using Stereoretentive Metathesis. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Q78K-7R18. https://resolver.caltech.edu/CaltechTHESIS:11202019-023320724

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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Natural Product; Total Synthesis; Olefin Metathesis
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Grubbs, Robert H. (advisor)
  • Stoltz, Brian M. (co-advisor)
Thesis Committee:
  • Reisman, Sarah E. (chair)
  • Agapie, Theodor
  • Grubbs, Robert H.
  • Stoltz, Brian M.
Defense Date:18 November 2019
Record Number:CaltechTHESIS:11202019-023320724
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:11202019-023320724
DOI:10.7907/Q78K-7R18
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.8b12816DOIArticle adapted for Chapter 1.
https://doi.org/10.1021/acs.orglett.6b02722DOIArticle adapted for Chapter 2.
ORCID:
AuthorORCID
Li, Jiaming0000-0001-6646-5693
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:13581
Collection:CaltechTHESIS
Deposited By: Jiaming Li
Deposited On:04 Dec 2019 18:39
Last Modified:26 May 2021 04:49

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