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Functional Group Transposition of Bicyclo[5.3.0]decadienones Afforded by the Allenic Pauson-Khand Reaction. An Approach Toward the Total Synthesis of (–)-Dehydroleucodine

Burchick, Joseph (2021) Functional Group Transposition of Bicyclo[5.3.0]decadienones Afforded by the Allenic Pauson-Khand Reaction. An Approach Toward the Total Synthesis of (–)-Dehydroleucodine. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

The allenic Pauson-Khand reaction (APKR) has proven to be a powerful method for the
construction of seven-membered rings. Despite this, only a few reports of this methodology being
employed in total syntheses exist. Reported herein are synthetic studies targeted towards the
elaboration of APKR adducts via the functionalization of the resulting enone motif. In addition, a
rapid synthetic route towards the core 5,7,5-framework of biologically active 6,12-guaianolides
was developed in an enantioselective fashion, utilizing the APKR as they key ring-forming step.
The successful APKR adduct functionalization studies were combined with this novel synthetic
route in an effort towards the first total synthesis of (–)-dehydroleucodine.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Burchick, Josephjburchick@gmail.comjob108
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairBrummond, Kaykbrummon@pitt.edukbrummon
Committee MemberFloreancig, Paulflorean@pitt.eduflorean
Committee MemberMcDermott, Leelam179@pitt.edulam179
Committee MemberLiu, Pengpengliu@pitt.edupengliu
Date: 20 January 2021
Date Type: Publication
Defense Date: 5 November 2020
Approval Date: 20 January 2021
Submission Date: 4 December 2020
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 293
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: allenic pauson-khand reaction, catalysis, total synthesis
Date Deposited: 20 Jan 2021 18:17
Last Modified: 20 Jan 2021 18:17
URI: http://d-scholarship.pitt.edu/id/eprint/40005

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