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Studies Towards the Total Synthesis of (+)-Retronecine and Anthracimycin

Smith, Joshua (2016) Studies Towards the Total Synthesis of (+)-Retronecine and Anthracimycin. PhD thesis, University of York.

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Abstract

This thesis consists of two separate projects. The first project involved an attempted total synthesis of (+)-retronecine A, a poisonous pyrrolizidine alkaloid via a novel asymmetric α-lithiation-substitution reaction of N-thiopivaloyl azetidine B, mediated by a chiral diamine. A total synthesis was not possible and our attention turned towards elucidating the mechanism of enantioinduction. Of particular note was how the use of carbon dioxide and methyl chloroformate as electrophiles gave products with the opposite configuration under otherwise identical reaction conditions (using (–)-sparteine C). Chapter two consists of work undertaken towards a total synthesis of anthracimycin D, a potent marine antibiotic. The development of robust methodology was explored for the early stages of the synthesis. In addition, a synthesis of the model decalinone E, was developed, via a Sakurai-aldol reaction, followed by ring closing metathesis.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Identification Number/EthosID: uk.bl.ethos.707483
Depositing User: Dr Joshua Smith
Date Deposited: 12 Apr 2017 14:41
Last Modified: 24 Jul 2018 15:22
URI: http://etheses.whiterose.ac.uk/id/eprint/16427

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