α-Boryl Ether Fragmentation via Boronate Oxidation for Cargo Release: The Total Synthesis of Simplified Analogues of Bistramide A

Hanna, Ramsey (2018) α-Boryl Ether Fragmentation via Boronate Oxidation for Cargo Release: The Total Synthesis of Simplified Analogues of Bistramide A. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

The first α-boryl ether molecular scaffold for the release of alcohols, aldehydes, and ketones in the presence of H2O2 is described. Utilizing novel chemistry that gives access to α-hydroxy boronates as well as methods for their successive etherification and acetalization, alcohols, aldehydes, and ketones can be released in vivo in the presence of exogenous and endogenous H2O2.
The synthesis of potent simplified analogues of Bistramide A, the primary cellular receptor for actin and a potent cytotoxin, have been synthesized in 9 steps, an improvement over the previous total synthesis of Bistramide A (14 steps). The key step in the synthesis was accomplished using a one pot hetero diels-alder reaction (HDA), 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation, and an acid mediated cyclization.

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Details

Item Type:	University of Pittsburgh ETD
Status:	Unpublished
Creators/Authors:	Creators Email Pitt Username ORCID Hanna, Ramsey ramsey.hanna1@gmail.com rdh41
ETD Committee:	Title Member Email Address Pitt Username ORCID Committee Chair Floreancig, Paul florean@pitt.edu Committee Member Li, Song kbrummon@pitt.edu Committee Member Brummond, Kay sol4@pitt.edu Committee Member Kazunori, Koide koide@pitt.edu
Date:	27 September 2018
Date Type:	Publication
Defense Date:	2 May 2018
Approval Date:	27 September 2018
Submission Date:	8 May 2018
Access Restriction:	No restriction; Release the ETD for access worldwide immediately.
Number of Pages:	245
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:	Boron Prodrug Organic Chemistry Bistramide Synthesis
Date Deposited:	27 Sep 2018 16:37
Last Modified:	27 Sep 2018 16:37
URI:	http://d-scholarship.pitt.edu/id/eprint/34492

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• α-Boryl Ether Fragmentation via Boronate Oxidation for Cargo Release: The Total Synthesis of Simplified Analogues of Bistramide A. (deposited 27 Sep 2018 16:37) [Currently Displayed]

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