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...
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University of Nottingham
1989
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ndltd-bl.uk-oai-ethos.bl.uk-3298532015-03-19T03:21:04ZThe synthesis of furofuranoid lignansStevens, David R.1989An 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.547QD241 Organic chemistryUniversity of Nottinghamhttp://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.329853http://eprints.nottingham.ac.uk/13170/Electronic Thesis or Dissertation |
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NDLTD |
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NDLTD |
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547 QD241 Organic chemistry |
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547 QD241 Organic chemistry Stevens, David R. The synthesis of furofuranoid lignans |
| 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. |
| author |
Stevens, David R. |
| author_facet |
Stevens, David R. |
| author_sort |
Stevens, David R. |
| title |
The synthesis of furofuranoid lignans |
| title_short |
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_sort |
synthesis of furofuranoid lignans |
| publisher |
University of Nottingham |
| publishDate |
1989 |
| url |
http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.329853 |
| work_keys_str_mv |
AT stevensdavidr thesynthesisoffurofuranoidlignans AT stevensdavidr synthesisoffurofuranoidlignans |
| _version_ |
1716732986704003072 |