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Synthetic Applications of the BHQ Reaction: Towards the Total Synthesis of Plumbagin

Wong, Michael Mun Chil

[Thesis]. Manchester, UK: The University of Manchester; 2015.

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Abstract

Plumbagin is a naturally occurring quinone which is well documented for having a plethora of beneficial medicinal properties. This report explores a synthetic preparation of the natural product through the use of the BHQ reaction, a unique and efficient benzannulation method which regiospecifically installs a halogen on the 4-position on the newly formed six-membered ring, during the course of a ten-step total synthesis.The synthetic route commences with 2-methyl hydroquinone and after subjugation to several chemical transformations 5-chloro-1,4-dimethoxy-2-methyl naphthalene was afforded supported by evidence from X-ray crystal diffraction analysis. Although the installed aryl chloride proved unsuitable for further chemical manipulation an alternative substrate, an aryl bromide, was produced and successfully displaced with a boronic ester providing a suitable functional precursor leading to the target compound however further attempts to isolate plumbagin from the by-products in the last step did not come to fruition.

Bibliographic metadata

Type of resource:
Content type:
Form of thesis:
Type of submission:
Degree type:
Master of Philosophy
Degree programme:
MPhil Chemistry
Publication date:
Location:
Manchester, UK
Total pages:
110
Abstract:
Plumbagin is a naturally occurring quinone which is well documented for having a plethora of beneficial medicinal properties. This report explores a synthetic preparation of the natural product through the use of the BHQ reaction, a unique and efficient benzannulation method which regiospecifically installs a halogen on the 4-position on the newly formed six-membered ring, during the course of a ten-step total synthesis.The synthetic route commences with 2-methyl hydroquinone and after subjugation to several chemical transformations 5-chloro-1,4-dimethoxy-2-methyl naphthalene was afforded supported by evidence from X-ray crystal diffraction analysis. Although the installed aryl chloride proved unsuitable for further chemical manipulation an alternative substrate, an aryl bromide, was produced and successfully displaced with a boronic ester providing a suitable functional precursor leading to the target compound however further attempts to isolate plumbagin from the by-products in the last step did not come to fruition.
Thesis main supervisor(s):
Thesis co-supervisor(s):
Language:
en

Institutional metadata

University researcher(s):

Record metadata

Manchester eScholar ID:
uk-ac-man-scw:261671
Created by:
Wong, Michael
Created:
25th March, 2015, 19:23:05
Last modified by:
Wong, Michael
Last modified:
16th November, 2017, 14:24:01

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