The University of Southampton
University of Southampton Institutional Repository

Towards the total syntheses of aspidospermidine and aspidofractinine: the curious chemistry of the indolinyl radical

Towards the total syntheses of aspidospermidine and aspidofractinine: the curious chemistry of the indolinyl radical
Towards the total syntheses of aspidospermidine and aspidofractinine: the curious chemistry of the indolinyl radical
This thesis is concerned with the total syntheses of the natural products aspidospermidine and aspidofractinine. These targets are noteworthy not only for the biological activity displayed within the class but also for their interesting molecular architecture. Herein, two routes towards the natural products are presented. Key features of the first route, a unified approach to both targets via the indolinyl radical, include the elegant construction of the core ABDE ring system, a mild lactam reduction and synthesis of the key cyclic imine. The second route features a highly efficient Stille coupling and a Wittig olefination. Attempts to effect a critical radical cyclisation reaction are also discussed. The chemistry of the C2 indolinyl radical is investigated, in particular the influence of the C3 indolinyl substitution upon the radical pathway followed. A discussion of the study and its findings is presented in Chapter 4. A review of synthetic approaches to these natural products since 2007 is presented in Chapter 1, in addition to details on their isolation, characterisation and biosynthesis, and an overview of their biological activity. Experimental procedures and characterisation data are provided in Chapter 6
Stenning, Kerri Joanne
b4a85a00-5d21-46f3-bbba-4ae3cef67944
Stenning, Kerri Joanne
b4a85a00-5d21-46f3-bbba-4ae3cef67944
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b

Stenning, Kerri Joanne (2011) Towards the total syntheses of aspidospermidine and aspidofractinine: the curious chemistry of the indolinyl radical. University of Southampton, Chemistry, Doctoral Thesis, 184pp.

Record type: Thesis (Doctoral)

Abstract

This thesis is concerned with the total syntheses of the natural products aspidospermidine and aspidofractinine. These targets are noteworthy not only for the biological activity displayed within the class but also for their interesting molecular architecture. Herein, two routes towards the natural products are presented. Key features of the first route, a unified approach to both targets via the indolinyl radical, include the elegant construction of the core ABDE ring system, a mild lactam reduction and synthesis of the key cyclic imine. The second route features a highly efficient Stille coupling and a Wittig olefination. Attempts to effect a critical radical cyclisation reaction are also discussed. The chemistry of the C2 indolinyl radical is investigated, in particular the influence of the C3 indolinyl substitution upon the radical pathway followed. A discussion of the study and its findings is presented in Chapter 4. A review of synthetic approaches to these natural products since 2007 is presented in Chapter 1, in addition to details on their isolation, characterisation and biosynthesis, and an overview of their biological activity. Experimental procedures and characterisation data are provided in Chapter 6

Text
K_Stenning_PhD_Thesis_2011.pdf - Other
Download (19MB)

More information

Published date: 30 September 2011
Organisations: University of Southampton, Chemistry

Identifiers

Local EPrints ID: 209099
URI: http://eprints.soton.ac.uk/id/eprint/209099
PURE UUID: c78e2b56-5436-42ff-b28d-fa6e8952bb02
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 26 Jan 2012 13:50
Last modified: 30 Jan 2020 01:27

Export record

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×