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FLUOROUS SYNTHESIS OF A TRI-β-PEPTIDE LIBRARY AND EIGHT STEREOISOMERS OF MACROLACTONE SCH725674

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Wang, Xiao (2009) FLUOROUS SYNTHESIS OF A TRI-β-PEPTIDE LIBRARY AND EIGHT STEREOISOMERS OF MACROLACTONE SCH725674. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

Chapter 1 of this dissertation describes a new strategy to make β-peptide libraries. A 27-membered tri-β-peptide library was prepared. β-Azido acids as building blocks were tagged with fluorous PMB group. Two reduction-amide coupling cycles were done. Intermediates were separated by Fluorous Solid Phase Extraction (FSPE). The reductive deprotection gave the final 27 tri-β-peptide, which were purified by reverse phase HPLC. Purity of the library was checked by LC-MS. Mass spectroscopy data of 25 products matched with calculation. Chapter 2 describes the Fluorous Mixture Synthesis (FMS) of eight stereoisomers of 14-membered macrolactone Sch725674. The configurations of Sch725674 were completely unknown when discovered. A single diastereomer of Sch725674 was prepared first by traditional solution phase synthesis. In the FMS, stereoisomeric starting materials were tagged with different fluorous TIPS groups. The tagged quasidiastereomers were mixed and the mixture underwent a series of steps to make the fluorous tagged macrolactones, which were separated by fluorous HPLC followed by individual deprotections to provide the eight final products. The NMR data of the eight synthetic macrolactones were compared with those of Sch725674. The absolute configuration of Sch725674 was confirmed as (4R,5S,7R,13R).


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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wang, Xiaoxiw25@pitt.edu,xiw25@yahoo.comXIW25
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran, Dennis P
Committee MemberDay, Billy W
Committee MemberFloreancig, Paul E
Committee MemberNelson, Scott G
Date: 25 June 2009
Date Type: Completion
Defense Date: 17 February 2009
Approval Date: 25 June 2009
Submission Date: 24 March 2009
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
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: β-Peptide; Fluorous Mixture Synthesis; Fluorous Solid Phase Extraction; Macrolactone; Sch725674
Other ID: http://etd.library.pitt.edu/ETD/available/etd-03242009-125753/, etd-03242009-125753
Date Deposited: 10 Nov 2011 19:32
Last Modified: 15 Nov 2016 13:37
URI: http://d-scholarship.pitt.edu/id/eprint/6579

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