A Synthesis of Theopederin D

Smith, Christopher (1998) A Synthesis of Theopederin D. PhD thesis, University of Glasgow.

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Abstract

A stereocontrolled synthesis of 18-O-methyl mycalamide B (1.5) and theopederin D (1.1d) is reported in this thesis. 18-O-Methyl mycalamide B (1.5) was synthesised first and the route was adapted enabling a synthesis of theopederin D (1.1d) to be completed. The synthesis of theopederin D (1.1d) included a metallated dihydropyran approach to couple the left fragment (1.72) and the right fragment (6.19) together and a reaction between oxirane (6.7) and a MOM ether to forge the cis-2,4,7-trioxabicyclo[4.4.0]decalin ring. An efficient large scale route was developed to provide substantial quanities of early intermediates of the right fragment (6.19) incorporating a highly enantioselective aymmetric reduction to generate beta-hydroxy ester (4.4) and a highly enantioselective asymmetric aldol reaction to also generate beta-hydroxy ester (4.4). A new highly diastereoselective synthesis of the left fragment (1.72) was developed starting from ethyl (S)-lactate (3.4). The absolute stereochemistry of an andvanced intermediate (6.20) was determined by X-ray crystallography.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Additional Information: Adviser: Philip J Kocienski
Keywords: Organic chemistry
Date of Award: 1998
Depositing User: Enlighten Team
Unique ID: glathesis:1998-74790
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 13 Nov 2019 15:58
Last Modified: 13 Nov 2019 15:58
URI: http://theses.gla.ac.uk/id/eprint/74790

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