The synthesis of furofuranoid lignans

Stevens, David R. (1989) The synthesis of furofuranoid lignans. PhD thesis, University of Nottingham.

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Abstract

An approach to the synthesis of 2,6-diaryl-8-oxo-3,7-dioxabicyclo [3,3,0] octane lignan lactones is presented and then used in the synthesis of the natural products aptosimon and styraxin. The structure of aptosimon has now been confirmed as having a 2,6-diaryl structure rather than the 2,4-diaryl structure which has been postulated in the literature. A germination inhibitor MEL, isolated from Aegilops ovata, has also been synthesised.

A key ring closing reaction in this strategy was a Lewis acid catalysed directed aldol reaction between a silyl enol ether and an acetal. A review of similar ring closures in the literature is presented.

The use of alpha-arylidene lactones as intermediates in lignin synthesis has also been investigated. The stereochemistry of products from reactions used in this strategy was determined and as a result it was possible to successfully design a stereochemically controlled synthesis of dihydrosesamin.

Item Type: Thesis (University of Nottingham only) (PhD)
Supervisors: Whiting, D.
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 13170
Depositing User: EP, Services
Date Deposited: 26 Mar 2013 13:36
Last Modified: 14 Sep 2016 03:34
URI: http://eprints.nottingham.ac.uk/id/eprint/13170

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