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Towards the Total Synthesis of Tetrafibricin

Gardner, Sean (2021) Towards the Total Synthesis of Tetrafibricin. Master's Thesis, University of Pittsburgh. (Unpublished)

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This work describes the continuation of the total synthesis of the marine natural product Tetrafibricin in the Curran Group. Retrosynthetic analysis of the framework of tetrafibricin lends to a convergent synthesis using 6 fragments: C1-C8, C9-C13, C14-C20, C21-C30, C31-C34 and C35-C40. Following the last attempt that yielded approximately 1 mg of fully protected tetrafibricin, this attempt features scale up and reaction selection improvements in order to provide enough of the fragments in order to realize the successful coupling strategy demonstrated in previous work. The synthesis was unsuccessful in that a material bottleneck occurred for the C21-C30 fragment, leading to the publication of the total synthesis by another academic group.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Gardner, Seansrg49@pitt.edusrg49
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran,
Committee MemberFloreancig,
Committee MemberWilcox,
Date: 8 October 2021
Date Type: Publication
Defense Date: 12 April 2021
Approval Date: 8 October 2021
Submission Date: 6 August 2021
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 124
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: Total synthesis natural product organic chemistry
Date Deposited: 08 Oct 2021 19:08
Last Modified: 08 Oct 2021 19:08

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