Mignone, James
(2005)
Cationic Zirconocene Mediated Cascade Synthesis of Tetrahydrofurans.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
Tetrahydrofurans and tetrahydropyrans are common structural features of numerous natural products, most notably the marine toxins and the polyether antibiotics, such brevetoxin and monensin. Despite the structural complexity of these two classes of compounds, a similarity arises when comparing the structural cores. The framework of all polyether antibiotics contains 2,5-disubstituted tetrahydrofurans, substituted tetrahydropyrans and spiroketal systems. A characteristic feature in the core of marine toxins is a trans-fused polycyclic ether moiety. Because of these similarities, it is believed that polycyclic ether compounds have a similar biogenetic origin, and many groups have postulated that Nature synthesizes these compounds via a polyene→polyepoxide→polyether pathway. Based on previous Wipf group methodology, enantiomerically pure diepoxide substrates with electronically differently ester terminating groups were subjected to 10 mol% Cp₂ZrCl₂ and 20 mol% AgClO₄. It was found that the 2-furyl and 2-benzofuryl ester moieties furnished the best yields and diastereoselectivities of the desired highly functionalized tetrahydrofurans.
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Details
Item Type: |
University of Pittsburgh ETD
|
Status: |
Unpublished |
Creators/Authors: |
|
ETD Committee: |
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Date: |
18 October 2005 |
Date Type: |
Completion |
Defense Date: |
20 April 2005 |
Approval Date: |
18 October 2005 |
Submission Date: |
26 July 2005 |
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: |
MS - Master of Science |
Thesis Type: |
Master's Thesis |
Refereed: |
Yes |
Uncontrolled Keywords: |
Peter Wipf; polyepoxide |
Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-07262005-184209/, etd-07262005-184209 |
Date Deposited: |
10 Nov 2011 19:53 |
Last Modified: |
15 Nov 2016 13:46 |
URI: |
http://d-scholarship.pitt.edu/id/eprint/8612 |
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