Chandra, Binita
(2010)
Catalytic Asymmetric Synthesis of Complex Polypropionates:A Synthesis of Erythronolide B.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
Studies towards the total synthesis of the polypropionate macrolide agycone Erythronolide B have been presented. Catalytic asymmetric AAC methodology has been applied to efficiently generate the C10-C13 and the C4-C5 stereocenters in the polypropionate fragments 105 and 209 through â-lactones 76, 80, and 86 respectively. An efficient installation of the C2 and C3-stereocenters in 193 was realized through a Lewis-base catalyzed Mukaiyama aldol reaction. Finally, a highly stereoselective aldol coupling of fragments 105 and 209 was used to join the fragments together.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
| Title | Member | Email Address | Pitt Username | ORCID |
|---|
| Committee Chair | Nelson, Scott | | | | | Committee Member | Doemling, Alexander | | | | | Committee Member | Wilcox, Craig S | | | | | Committee Member | Meyer, Tara | | | |
|
| Date: |
28 January 2010 |
| Date Type: |
Completion |
| Defense Date: |
8 December 2009 |
| Approval Date: |
28 January 2010 |
| Submission Date: |
15 November 2009 |
| Access Restriction: |
5 year -- Restrict access to University of Pittsburgh for a period of 5 years. |
| 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: |
macrolide synthesis; polypropionates; stereotetrad; AAC; erythronolide B |
| Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-11152009-132712/, etd-11152009-132712 |
| Date Deposited: |
10 Nov 2011 20:04 |
| Last Modified: |
15 Nov 2016 13:51 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/9681 |
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