Gopalarathnam, Apsara
(2007)
Efforts Towards the Total Synthesis of Amphidinolide B.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
Studies towards the total synthesis of the cytotoxic marine macrolide Amphidinolide B have been disclosed. Catalytic asymmetric AAC methodology has been applied to efficiently generate the C11- and the C18- stereocenters in the requisite fragments 114 and 120 throughƒnbeta-lactones 102 and 81 respectively.An efficient route to install the C14-C15 trisubstituted alkene was realized through a stannylcupration reaction. The Stille and Suzuki cross-coupling methodologies were investigated for the formation of the C13-C15 diene of amphidinolide B. Iodide 90 was coupled with boronic ester 114 via an efficient Suzuki reaction to form a C7-C20 fragment 115. Fragment was further homologated and coupled to sulfone 65 to complete a C1-C20 synthon of amphidinolide B.
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Details
Item Type: |
University of Pittsburgh ETD
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Status: |
Unpublished |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
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Gopalarathnam, Apsara | apg16@pitt.edu | APG16 | |
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ETD Committee: |
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Date: |
29 January 2007 |
Date Type: |
Completion |
Defense Date: |
5 September 2006 |
Approval Date: |
29 January 2007 |
Submission Date: |
7 September 2006 |
Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
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: |
cytotoxic activity; exocyclic diene |
Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-09072006-203459/, etd-09072006-203459 |
Date Deposited: |
10 Nov 2011 20:01 |
Last Modified: |
15 Nov 2016 13:50 |
URI: |
http://d-scholarship.pitt.edu/id/eprint/9337 |
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