The synthesis of furofuranoid lignans
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 s...
| Main Author: | |
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
1989
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| Online Access: | https://eprints.nottingham.ac.uk/13170/ |
| _version_ | 1848791669320712192 |
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| author | Stevens, David R. |
| author_facet | Stevens, David R. |
| author_sort | Stevens, David R. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T18:32:11Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-13170 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T18:32:11Z |
| publishDate | 1989 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-131702025-02-28T11:23:35Z https://eprints.nottingham.ac.uk/13170/ The synthesis of furofuranoid lignans Stevens, David R. 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. 1989 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/13170/1/329853.pdf Stevens, David R. (1989) The synthesis of furofuranoid lignans. PhD thesis, University of Nottingham. |
| spellingShingle | Stevens, David R. The synthesis of furofuranoid lignans |
| title | The synthesis of furofuranoid lignans |
| title_full | The synthesis of furofuranoid lignans |
| title_fullStr | The synthesis of furofuranoid lignans |
| title_full_unstemmed | The synthesis of furofuranoid lignans |
| title_short | The synthesis of furofuranoid lignans |
| title_sort | synthesis of furofuranoid lignans |
| url | https://eprints.nottingham.ac.uk/13170/ |