Lang, Feng
(2018)
Enantioenriched Oxazolidinones as Synthesis Scaffolds and Efforts towards the Total Synthesis of Marineosin A.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
Enantioenriched Oxazolidinones as Synthesis Scaffolds and
Efforts towards the Total Synthesis of Marineosin
Feng Lang, PhD
University of Pittsburgh, 2018
The utility of enantioenriched oxazolidinones in the preparation of small chiral building blocks has been investigated. Hard nucleophile induced ring opening reactions of oxazolidinones provided a series of enantioenriched α-hydroxy carbonyl compounds. Soft nucleophile induced ring opening reactions of oxazolidinones have been attempted. Aldol reactions and Mannich reactions of oxazolidinones afforded the addition products with good results. Additionally, the aldol addition products were able to be converted to enantioenriched α,β-dihydroxy carbonyl compounds with a quaternary chirality center at the α position. In addition, chiral diol was also obtained through the reductive ring opening reaction of oxazolidinone.
The synthesis of marineosin A, a structurally unique natural product exhibiting acute cytotoxicity, has been under investigation in our laboratory. The previously unreported spiroaminal structure consisting of tetrahydropyrrole ring and dihydropyran ring has been synthesized through a radical cyclization in model study. The 12-membered macrocyclic pyrrole core synthesis has been accomplished by Stetter reaction in model study. It is worth noting that this is the first time that Stetter reaction was used in macrocyclization reaction. Both the diene fragment and the dienophile fragment have been prepared successfully towards the synthesis of the densely functionalized tetrahydropyran ring in marineosin A.
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| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
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| Date: |
28 June 2018 |
| Date Type: |
Publication |
| Defense Date: |
29 March 2018 |
| Approval Date: |
28 June 2018 |
| Submission Date: |
8 April 2018 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| Number of Pages: |
152 |
| 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: |
Oxazolidinones; Methodology; Asymmetric synthesis; Marineosin A; Total synthesis |
| Date Deposited: |
28 Jun 2018 15:37 |
| Last Modified: |
28 Jun 2018 15:37 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/34185 |
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