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Cationic Zirconocene Mediated Cascade Synthesis of Tetrahydrofurans

Mignone, James (2005) Cationic Zirconocene Mediated Cascade Synthesis of Tetrahydrofurans. Master's Thesis, University of Pittsburgh. (Unpublished)

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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Status: Unpublished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:
CreatorsEmailPitt UsernameORCID
Mignone, Jamesjmignone80@hotmail.com
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Committee MemberNelson, Scottsgnelson@pitt.eduSGNELSON
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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