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Indanones: resolutions and reactions
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Earl, Matthew W. M. (2019) Indanones: resolutions and reactions. PhD thesis, University of Warwick.
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WRAP_Theses_Earl_2019.pdf - Submitted Version - Requires a PDF viewer. Download (6Mb) | Preview |
Official URL: http://webcat.warwick.ac.uk/record=b3493082~S15
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 (PhD) | ||||
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| Subjects: | Q Science > QD Chemistry | ||||
| Library of Congress Subject Headings (LCSH): | Indandione, Arylindandiones -- Synthesis, Chirality, Beckmann rearrangement, Schmidt reaction | ||||
| Official Date: | December 2019 | ||||
| Dates: |
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| 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: | |||||
| Extent: | xiv, 302 leaves : illustrations | ||||
| Language: | eng |
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