Skip to content Skip to navigation
University of Warwick
  • Study
  • |
  • Research
  • |
  • Business
  • |
  • Alumni
  • |
  • News
  • |
  • About

University of Warwick
Publications service & WRAP

Highlight your research

  • WRAP
    • Home
    • Search WRAP
    • Browse by Warwick Author
    • Browse WRAP by Year
    • Browse WRAP by Subject
    • Browse WRAP by Department
    • Browse WRAP by Funder
    • Browse Theses by Department
  • Publications Service
    • Home
    • Search Publications Service
    • Browse by Warwick Author
    • Browse Publications service by Year
    • Browse Publications service by Subject
    • Browse Publications service by Department
    • Browse Publications service by Funder
  • Help & Advice
University of Warwick

The Library

  • Login
  • Admin

Indanones: resolutions and reactions

Tools
- Tools
+ Tools

Earl, Matthew W. M. (2019) Indanones: resolutions and reactions. PhD thesis, University of Warwick.

[img]
Preview
PDF
WRAP_Theses_Earl_2019.pdf - Submitted Version - Requires a PDF viewer.

Download (6Mb) | Preview
Official URL: http://webcat.warwick.ac.uk/record=b3493082~S15

Request Changes to record.

Abstract

Chiral 3-aryl-indan-1-ones are incredibly useful compounds; they not only occur as the primary pharmacophore of a wide array of drugs and natural products, but also serve as building blocks towards medicinal scaffolds and other attractive compounds. There are countless examples of indan-1-ones exhibiting considerable medicinal properties, however often only the racemate is reported in such cases. This thesis describes the development of a general route for the synthesis of enantiomerically enriched 3-arylindan- 1-ones and their subsequent transformations into a range of interesting compounds.

Chapter 1 provides an introduction to indan-1-ones – in particular those bearing a pendant 3-aryl group – and an insight into their biological importance. Asymmetric approaches towards these species are briefly examined, with a focus on the different resolution techniques that are available. This is followed by a more thorough discussion on oxidative kinetic resolutions of secondary alcohols, which serves as an avenue towards enantioenriched 3-aryl-indan-1-ones.

A convenient synthetic route that allows access to the individual enantiomers of 3-arylindan- 1-ones in high enantiomeric excesses is discussed in Chapter 2. To begin, the straightforward synthesis of a series of racemic 3-aryl-indan-1-ones from commercially available starting materials is communicated. Following this is a “2.5-step” resolution of these racemic species into their individual enantiomers, the principal step being a highly stereospecific ruthenium-catalysed oxidative kinetic resolution.

Chapter 3 demonstrates the usefulness of 3-aryl-indan-1-ones as building blocks towards a variety of interesting medicinal scaffolds. The chapter opens with a survey of the biological properties of these compounds, after which two ring expansion transformations of 3-aryl-indan-1-ones – the Beckmann rearrangement and Schmidt reaction – are investigated. Further manipulations towards additional compounds of medicinal interest are then described, followed by the facile transformation of 3-aryl-indan-1-ones into their biologically active benzylidene counterparts. The syntheses of both enantiomers of two highly bioactive synthetic targets are also presented herein.

Item Type: Thesis or Dissertation (PhD)
Subjects: Q Science > QD Chemistry
Library of Congress Subject Headings (LCSH): Indandione, Arylindandiones -- Synthesis, Chirality, Beckmann rearrangement, Schmidt reaction
Official Date: December 2019
Dates:
DateEvent
December 2019UNSPECIFIED
Institution: University of Warwick
Theses Department: Department of Chemistry
Thesis Type: PhD
Publication Status: Unpublished
Supervisor(s)/Advisor: Fox, David J. (David John)
Format of File: pdf
Extent: xiv, 302 leaves : illustrations
Language: eng

Request changes or add full text files to a record

Repository staff actions (login required)

View Item View Item

Downloads

Downloads per month over past year

View more statistics

twitter

Email us: wrap@warwick.ac.uk
Contact Details
About Us