Caplan, Scott
(2019)
Total Synthesis of Divergolides E and H and an Investigation into the Oxidative Rearrangement to Divergolides C and D.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
This thesis describes the first total syntheses of divergolides E and H. Construction of the core bridged bicyclic acetal unit was accomplished using a hetero-Diels–Alder (HDA) reaction and oxidative carbon-hydrogen bond cleavage to couple two highly functionalized subunits. Additional highlights of this convergent synthesis include a chelation-controlled alkenylzinc addition, amide formation between a hindered aniline and an acylating agent prone to ketene formation, and a challenging macrolactonization. Model studies showed effective oxidation of the core structure using a hypervalent iodine species which sets the stage for rearrangement into divergolides C and D.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
|
| Date: |
30 January 2019 |
| Date Type: |
Publication |
| Defense Date: |
4 December 2018 |
| Approval Date: |
30 January 2019 |
| Submission Date: |
20 November 2018 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| Number of Pages: |
206 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
PhD - Doctor of Philosophy |
| Thesis Type: |
Doctoral Dissertation |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
natural products, cycloadditions, macrocycles, oxidation, oxygen heterocycles |
| Date Deposited: |
30 Jan 2019 21:24 |
| Last Modified: |
30 Jan 2019 21:24 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/35517 |
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