Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds
The stunning advances in understanding the reactivity and selectivity principles of asymmetric pericyclic reactions have had a profound impact on the synthetic planning of complex natural products. Indeed, electrocyclizations, cycloadditions, and sigmatropic rearrangements enable synthetic chemists...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-10-01
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| Series: | Organics |
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| Online Access: | https://www.mdpi.com/2673-401X/2/4/21 |
| _version_ | 1797501740201803776 |
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| author | Stéphane P. Roche |
| author_facet | Stéphane P. Roche |
| author_sort | Stéphane P. Roche |
| collection | DOAJ |
| description | The stunning advances in understanding the reactivity and selectivity principles of asymmetric pericyclic reactions have had a profound impact on the synthetic planning of complex natural products. Indeed, electrocyclizations, cycloadditions, and sigmatropic rearrangements enable synthetic chemists to craft highly functionalized scaffolds that would not otherwise be possible with a similar atom-, step-, and redox-economy. In this review, selected examples from the last two decades of research (2003–2020) on tandem processes combining oxa-6π electrocyclic reactions are discussed in terms of reactivity challenges, inherent reversibility, and key structural bond formation in the assembly of natural products. A particular emphasis is given to the electrocyclic ring-closures in the tandem processes featuring Knoevenagel-type condensations, Diels–Alder cycloadditions, Stille couplings, and oxidative dearomatizations. The synthetic manifolds reviewed here illustrate how oxa-6π electrocyclizations are intimately linked to the construction of complex natural product scaffolds and have inspired a number of biomimetic syntheses in the laboratory. |
| first_indexed | 2024-03-10T03:22:54Z |
| format | Article |
| id | doaj.art-e34854fd418c4d278e7e33db49186a17 |
| institution | Directory Open Access Journal |
| issn | 2673-401X |
| language | English |
| last_indexed | 2024-03-10T03:22:54Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Organics |
| spelling | doaj.art-e34854fd418c4d278e7e33db49186a172023-11-23T10:00:00ZengMDPI AGOrganics2673-401X2021-10-012437638710.3390/org2040021Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product ScaffoldsStéphane P. Roche0Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431, USAThe stunning advances in understanding the reactivity and selectivity principles of asymmetric pericyclic reactions have had a profound impact on the synthetic planning of complex natural products. Indeed, electrocyclizations, cycloadditions, and sigmatropic rearrangements enable synthetic chemists to craft highly functionalized scaffolds that would not otherwise be possible with a similar atom-, step-, and redox-economy. In this review, selected examples from the last two decades of research (2003–2020) on tandem processes combining oxa-6π electrocyclic reactions are discussed in terms of reactivity challenges, inherent reversibility, and key structural bond formation in the assembly of natural products. A particular emphasis is given to the electrocyclic ring-closures in the tandem processes featuring Knoevenagel-type condensations, Diels–Alder cycloadditions, Stille couplings, and oxidative dearomatizations. The synthetic manifolds reviewed here illustrate how oxa-6π electrocyclizations are intimately linked to the construction of complex natural product scaffolds and have inspired a number of biomimetic syntheses in the laboratory.https://www.mdpi.com/2673-401X/2/4/21biomimetic synthesisnatural productsoxa-6π electrocyclic reactionsprivileged scaffoldstransannular reactions |
| spellingShingle | Stéphane P. Roche Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds Organics biomimetic synthesis natural products oxa-6π electrocyclic reactions privileged scaffolds transannular reactions |
| title | Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds |
| title_full | Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds |
| title_fullStr | Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds |
| title_full_unstemmed | Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds |
| title_short | Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds |
| title_sort | recent advances in oxa 6π electrocyclization reactivity for the synthesis of privileged natural product scaffolds |
| topic | biomimetic synthesis natural products oxa-6π electrocyclic reactions privileged scaffolds transannular reactions |
| url | https://www.mdpi.com/2673-401X/2/4/21 |
| work_keys_str_mv | AT stephaneproche recentadvancesinoxa6pelectrocyclizationreactivityforthesynthesisofprivilegednaturalproductscaffolds |