Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach
Bestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β,γ,δ-unsaturated esters (dienoates) is achiev...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.11.197 |
| _version_ | 1818577667746693120 |
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| author | Jingjing Wang Samuel Z. Y. Ting Joanne E. Harvey |
| author_facet | Jingjing Wang Samuel Z. Y. Ting Joanne E. Harvey |
| author_sort | Jingjing Wang |
| collection | DOAJ |
| description | Bestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β,γ,δ-unsaturated esters (dienoates) is achieved through the coupling of Bestmann ylide, an alcohol and an α,β-unsaturated aldehyde. Primary and secondary alcohols, including allylic alcohols, are suitable substrates; the newly formed alkene has an E-geometry. Strategically, this represents a highly efficient route to unsaturated polyketide derivatives. A linchpin approach to the synthesis of a major fragment of the natural products zampanolide and dactylolide is investigated using Bestmann ylide to link the C16–C20 alcohol with the C3–C8 aldehyde fragment. |
| first_indexed | 2024-12-16T06:33:34Z |
| format | Article |
| id | doaj.art-b9e5fbe88ced40d09201939a59f70a6c |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T06:33:34Z |
| publishDate | 2015-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-b9e5fbe88ced40d09201939a59f70a6c2022-12-21T22:40:51ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-10-011111815182210.3762/bjoc.11.1971860-5397-11-197Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approachJingjing Wang0Samuel Z. Y. Ting1Joanne E. Harvey2Centre for Biodiscovery, School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New ZealandCentre for Biodiscovery, School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New ZealandCentre for Biodiscovery, School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New ZealandBestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β,γ,δ-unsaturated esters (dienoates) is achieved through the coupling of Bestmann ylide, an alcohol and an α,β-unsaturated aldehyde. Primary and secondary alcohols, including allylic alcohols, are suitable substrates; the newly formed alkene has an E-geometry. Strategically, this represents a highly efficient route to unsaturated polyketide derivatives. A linchpin approach to the synthesis of a major fragment of the natural products zampanolide and dactylolide is investigated using Bestmann ylide to link the C16–C20 alcohol with the C3–C8 aldehyde fragment.https://doi.org/10.3762/bjoc.11.197Bestmann ylidedactylolidedienoate(triphenylphosphoranylidene)ketenezampanolide |
| spellingShingle | Jingjing Wang Samuel Z. Y. Ting Joanne E. Harvey Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach Beilstein Journal of Organic Chemistry Bestmann ylide dactylolide dienoate (triphenylphosphoranylidene)ketene zampanolide |
| title | Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach |
| title_full | Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach |
| title_fullStr | Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach |
| title_full_unstemmed | Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach |
| title_short | Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach |
| title_sort | preparation of conjugated dienoates with bestmann ylide towards the synthesis of zampanolide and dactylolide using a facile linchpin approach |
| topic | Bestmann ylide dactylolide dienoate (triphenylphosphoranylidene)ketene zampanolide |
| url | https://doi.org/10.3762/bjoc.11.197 |
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