Stereoselective strategies to access spirotetronate natural products
Spirotetronates constitute a large family of natural products that have attracted significant attention due to their intriguing structures and broad biological activities. These compounds share a common spirocyclic 4-hydroxy-1-oxaspiro[4.5]deca-3,7-dien-2-one unit, whose synthesis has been actively...
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| Format: | Article |
| Language: | English |
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Académie des sciences
2024-12-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.352/ |
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| author | Brion, Aurélien Neuville, Luc Masson, Géraldine |
| author_facet | Brion, Aurélien Neuville, Luc Masson, Géraldine |
| author_sort | Brion, Aurélien |
| collection | DOAJ |
| description | Spirotetronates constitute a large family of natural products that have attracted significant attention due to their intriguing structures and broad biological activities. These compounds share a common spirocyclic 4-hydroxy-1-oxaspiro[4.5]deca-3,7-dien-2-one unit, whose synthesis has been actively pursued by chemists. In this review, we highlight various approaches to accessing diversely substituted spirotetronates, including methods that enable the total synthesis of selected natural targets. The Diels–Alder/Dieckmann route originally reported has been extensively developed and encompasses various diastereoselective processes. Although enantioselective transformations have been reported, they remain scarce. Additionally, although less explored, alkylation of ketones has been employed for the synthesis of alkoxyfuran-2(5H)-one scaffolds, and selected ring-forming strategies have been investigated to construct pre-functionalized cyclohexyl backbones. |
| format | Article |
| id | doaj-art-bf49b5a60fbe4f0ebc15d8c01f3ee18d |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-bf49b5a60fbe4f0ebc15d8c01f3ee18d2025-02-07T13:39:46ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432024-12-0127G131934110.5802/crchim.35210.5802/crchim.352Stereoselective strategies to access spirotetronate natural productsBrion, Aurélien0https://orcid.org/0000-0002-4686-5865Neuville, Luc1https://orcid.org/0000-0002-4648-2469Masson, Géraldine2https://orcid.org/0000-0003-2333-7047Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, Gif-sur-Yvette Cedex 91198, FranceHitCat, Seqens-CNRS Joint Laboratory, Seqens’Lab, 8 Rue de Rouen, Porcheville 78440, France; Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, Gif-sur-Yvette Cedex 91198, FranceHitCat, Seqens-CNRS Joint Laboratory, Seqens’Lab, 8 Rue de Rouen, Porcheville 78440, France; Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, Gif-sur-Yvette Cedex 91198, FranceSpirotetronates constitute a large family of natural products that have attracted significant attention due to their intriguing structures and broad biological activities. These compounds share a common spirocyclic 4-hydroxy-1-oxaspiro[4.5]deca-3,7-dien-2-one unit, whose synthesis has been actively pursued by chemists. In this review, we highlight various approaches to accessing diversely substituted spirotetronates, including methods that enable the total synthesis of selected natural targets. The Diels–Alder/Dieckmann route originally reported has been extensively developed and encompasses various diastereoselective processes. Although enantioselective transformations have been reported, they remain scarce. Additionally, although less explored, alkylation of ketones has been employed for the synthesis of alkoxyfuran-2(5H)-one scaffolds, and selected ring-forming strategies have been investigated to construct pre-functionalized cyclohexyl backbones.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.352/SpirotetronatesDiels–Alder reactionStereoselective synthesisTotal synthesis |
| spellingShingle | Brion, Aurélien Neuville, Luc Masson, Géraldine Stereoselective strategies to access spirotetronate natural products Comptes Rendus. Chimie Spirotetronates Diels–Alder reaction Stereoselective synthesis Total synthesis |
| title | Stereoselective strategies to access spirotetronate natural products |
| title_full | Stereoselective strategies to access spirotetronate natural products |
| title_fullStr | Stereoselective strategies to access spirotetronate natural products |
| title_full_unstemmed | Stereoselective strategies to access spirotetronate natural products |
| title_short | Stereoselective strategies to access spirotetronate natural products |
| title_sort | stereoselective strategies to access spirotetronate natural products |
| topic | Spirotetronates Diels–Alder reaction Stereoselective synthesis Total synthesis |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.352/ |
| work_keys_str_mv | AT brionaurelien stereoselectivestrategiestoaccessspirotetronatenaturalproducts AT neuvilleluc stereoselectivestrategiestoaccessspirotetronatenaturalproducts AT massongeraldine stereoselectivestrategiestoaccessspirotetronatenaturalproducts |