Enantioselective synthesis of pretomanid & investigations of Raman spectroscopy for through-tube monitoring of reactions

Chapter 1: Enantioselective Synthesis of Pretomanid [color illustrations] Pretomanid is a potential cornerstone active pharmaceutical ingredient for the treatment of tuberculosis (TB). It is found in several advanced clinical trials and can possibly treat all forms of TB. In this report, we discuss the development of a novel synthesis of pretomanid through a selective epoxide-opening cyclization and late-stage nitration. This route offers a new strategy to access the core of pretomanid and avoids the necessity of the explosive starting material. Chapter 2: Investigations of Raman Spectroscopy for Through-Tube Monitoring of Reactions [color illustrations] Continuous-flow chemistry has seen expansive growth and thus requires powerful new analytical techniques. The current commonly-used analytics involve inline analysis at a single point, which can hinder analysis. In this report, we demonstrate the utility of the MarqMetrix TouchRaman probe for reaction monitoring through a continuous-flow reactor. The reactions studied were ring-closing metathesis, benzyne generation, and ketene generation.

Name thesis:degree_name

Doctoral

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2019

Author dc:creator

• Tran, Tho Huu.

Advisor dc:contributor.advisor

• Timothy F. Jamison.

• Chemistry.

Statement dc:rights

• MIT theses are protected by copyright. They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/1721.1/122857

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/122857