White Rose University Consortium logo
University of Leeds logo University of Sheffield logo York University logo

Studies towards the total synthesis of 'upenamide

Gallagher, Katherine (2011) Studies towards the total synthesis of 'upenamide. PhD thesis, University of York.

full for soft.pdf
Available under License Creative Commons Attribution-Noncommercial-No Derivative Works 2.0 UK: England & Wales.

Download (22Mb)


Synthetic studies towards the total synthesis of the macrocyclic marine alkaloid ‘upenamide (I) are reported. After an introduction (Chapter 1), Chapter 2 describes an extension of some methodology utilised during the total synthesis project. Both the polycyclic ABC and DE core units of ’upenamide were formed by a stannous chloride dihydrate mediated cyclisation reaction and the methodology described involves using stannous chloride dihydrate to deliver novel polycyclic heterocycles, for example II, III and IV. In Chapter 3, a shortened synthetic route to the ABC core unit V is described, using a novel azide as a protected amine. A route to the DE core unit VI was developed and is described in Chapter 4. Chapter 5 describes the coupling of the DE core unit VI with the ABC core unit precursor VII, giving the ABC and DE cores joined through the fully saturated chain in the advanced intermediate VIII. Chapter 5 also contains a discussion of future research needed to complete the program of research into ’upenamide.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Identification Number/EthosID: uk.bl.ethos.542834
Depositing User: Miss Katherine Gallagher
Date Deposited: 29 Sep 2011 14:38
Last Modified: 08 Sep 2016 12:20
URI: http://etheses.whiterose.ac.uk/id/eprint/1639

You do not need to contact us to get a copy of this thesis. Please use the 'Download' link(s) above to get a copy.
You can contact us about this thesis. If you need to make a general enquiry, please see the Contact us page.

Actions (repository staff only: login required)