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Rearrangement and Cascade Reactions: New Synthetic Methods and the Total Synthesis of Diazonamide A

Waller, David Lee (2008) Rearrangement and Cascade Reactions: New Synthetic Methods and the Total Synthesis of Diazonamide A. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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This dissertation describes the development of several cascade reactions and their application to the synthesis of structurally and/or biologically relevant molecules. We successfully developed a three-step, one-pot carboalumination-Claisen rearrangement-addition reaction, which provides complex allylic alcohols from simple starting materials. While attempting to extend this methodology to nitrogen-containing substrates, a tandem hydrozirconation-iminium ion addition reaction was developed that allows simple access to functionalized isoindolinones. An oxidative rearrangement of enol ethers to spiroketals was developed, contributing an unusual approach to these highly sought after functionalities. Finally, an approach to the complex natural product diazonamide A was investigated with the intention of applying the Chan rearrangement. Eventually, the complexities of total synthesis forbid the use of the Chan rearrangement, and an alternative pathway was developed that led to the application of a cascade acyl chloride-oxazoline ring scission to install critical components of diazonamide.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Waller, David Leedlw55@pitt.eduDLW55
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberLazo, Johnlazo@pitt.eduLAZO
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Committee MemberNelson, Scott G.sgnelson@pitt.eduSGNELSON
Date: 16 June 2008
Date Type: Completion
Defense Date: 13 February 2008
Approval Date: 16 June 2008
Submission Date: 21 February 2008
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: cascade reaction; diazonamide; heck reaction; isoindolinone; oxazole; spiroketal
Other ID:, etd-02212008-154234
Date Deposited: 10 Nov 2011 19:31
Last Modified: 15 Nov 2016 13:36


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