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Efforts towards the Macrocyclic Core of Marineosin A and Development of Pyrrolidine-Based Scaffolds for Diversity-Oriented Synthesis

Perez, Rachel (2015) Efforts towards the Macrocyclic Core of Marineosin A and Development of Pyrrolidine-Based Scaffolds for Diversity-Oriented Synthesis. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

The total synthesis of marineosin A, a unique spiroaminal with selective cytotoxicity, has been under investigation in our laboratory. A ruthenium-catalyzed enolate allylic alkylation methodology and azafulvene dimer-derived metathesis strategy have been considered as potential routes, towards the synthesis of the macrocyclic core of marineosin A.

A novel route to the synthesis of diverse pyrrolidine scaffolds, for diversity-oriented synthesis has additionally been under investigation in our laboratory. The synthetic route encompasses a series of reductive amination, iodocyclization, azide substitution, and reductive deprotection to deliver the target diamine scaffolds in 14-16% yield. In addition, an asymmetric approach to the synthesis of (2S,3R,4R)-β–iodo amine has been presented, which takes advantage of selective Ru(II)-catalyzed Claisen rearrangement methodology.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Perez, Rachelrap52@pitt.eduRAP52
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scottsgnelson@pitt.eduSGNELSON
Committee MemberGold, Barrygoldbi@pitt.eduGOLDBI
Committee MemberHorne, Sethhorne@pitt.eduHORNE
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Date: 27 September 2015
Date Type: Publication
Defense Date: 13 May 2015
Approval Date: 27 September 2015
Submission Date: 9 April 2015
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 127
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: Diversity-Oriented Synthesis, Marineosin A, spiroaminal, ruthenium-catalyzed enolate allylic alkylation, pyrrolidine scaffolds.
Date Deposited: 28 Sep 2015 00:43
Last Modified: 15 Nov 2016 14:27
URI: http://d-scholarship.pitt.edu/id/eprint/24699

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