Structural and synthetic studies in insect chemistry
Structural and synthetic studies in insect chemistry
Chemical analysis of extracts of larch sawfly, Cephalcia lariciphilia females identified o-aminoacetophenone as a component of the sex pheromone. o-Aminoacetophenone was found to release 'activation' in males. Electroantennography and behavioural studies indicated the presence of other pheromone components. (E)-6-Farnesene was identified in six British aphid species: Myzus persicae, Aphis fabae, Acyrthosiphon pisum, Metopolophium dirodum, Rhopalosiphum padi and Sitobion avenae Analysis of Aphis fabae extracts revealed the presence of some minor chemical components including two sesquiterpenes and tetradecanyl acetate.3,4,4,7-Tetramethyl-6-octen-l-ol, formerly thought to be a component of the cephalic secretion of the solitary bee Andrena wilKella, was synthesised by a route utilising 3,3,6-trimethyl-5-hepten-2-one as the key intermediate. Comparison of the mass spectrum of the alcohol with that of the natural product demonstrated that 3,4,4,7-tetramethyl-6octen-l-ol was not the natural product. A synthetic route to pinguisone, 4,4a,6,7,7a,8-hexahydro-4,4a,7,7atstram'ithyl-5H-indeno(5,6-bIfuran-5-one, utilising annelation reactions (if. metiyl 5-oxo-3,4-dimethylcyclopentene-l-carboxylate was explored. Diels-Alder reactions were found to be unsuitable for construction of the indane skeleton. An annelation procedure involving two successive Michael additions of a lithium dienolate was used for the synthesis of a compound with the correct indane skeleton.
University of Southampton
1982
Selwood, David Lawrence
(1982)
Structural and synthetic studies in insect chemistry.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
Chemical analysis of extracts of larch sawfly, Cephalcia lariciphilia females identified o-aminoacetophenone as a component of the sex pheromone. o-Aminoacetophenone was found to release 'activation' in males. Electroantennography and behavioural studies indicated the presence of other pheromone components. (E)-6-Farnesene was identified in six British aphid species: Myzus persicae, Aphis fabae, Acyrthosiphon pisum, Metopolophium dirodum, Rhopalosiphum padi and Sitobion avenae Analysis of Aphis fabae extracts revealed the presence of some minor chemical components including two sesquiterpenes and tetradecanyl acetate.3,4,4,7-Tetramethyl-6-octen-l-ol, formerly thought to be a component of the cephalic secretion of the solitary bee Andrena wilKella, was synthesised by a route utilising 3,3,6-trimethyl-5-hepten-2-one as the key intermediate. Comparison of the mass spectrum of the alcohol with that of the natural product demonstrated that 3,4,4,7-tetramethyl-6octen-l-ol was not the natural product. A synthetic route to pinguisone, 4,4a,6,7,7a,8-hexahydro-4,4a,7,7atstram'ithyl-5H-indeno(5,6-bIfuran-5-one, utilising annelation reactions (if. metiyl 5-oxo-3,4-dimethylcyclopentene-l-carboxylate was explored. Diels-Alder reactions were found to be unsuitable for construction of the indane skeleton. An annelation procedure involving two successive Michael additions of a lithium dienolate was used for the synthesis of a compound with the correct indane skeleton.
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Published date: 1982
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Local EPrints ID: 459917
URI: http://eprints.soton.ac.uk/id/eprint/459917
PURE UUID: 075d380c-1b6b-42c8-ab08-8b0bac5db522
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Date deposited: 04 Jul 2022 17:27
Last modified: 04 Jul 2022 17:27
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Author:
David Lawrence Selwood
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