Bispericyclic Diels–Alder Dimerization of ortho ‐Quinols in Natural Product (Bio)Synthesis: Bioinspired Chemical 6‐Step Synthesis of (+)‐Maytenone
| العنوان: | Bispericyclic Diels–Alder Dimerization of ortho ‐Quinols in Natural Product (Bio)Synthesis: Bioinspired Chemical 6‐Step Synthesis of (+)‐Maytenone |
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| المؤلفون: | Mourad El Assal, Cyril Bosset, Anaëlle Cornu, Isabelle Chataigner, Denis Deffieux, Laurent Pouységu, Frédéric Castet, Romain Coffinier, Philippe A. Peixoto, Stéphane Quideau |
| المصدر: | Angewandte Chemie International Edition. 60:14967-14974 |
| بيانات النشر: | Wiley, 2021. |
| سنة النشر: | 2021 |
| مصطلحات موضوعية: | Biological Products, Natural product, Cycloaddition Reaction, Molecular Structure, 010405 organic chemistry, Enantioselective synthesis, Regioselectivity, Total synthesis, Stereoisomerism, General Chemistry, Quinolones, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Chemical synthesis, Catalysis, Transition state, Cycloaddition, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Stereoselectivity, Dimerization |
| الوصف: | Many natural products of plant or microbial origins are derived from enzymatic dearomative oxygenation of 2-alkylphenolic precursors into 6-alkyl-6-hydroxycyclohexa-2,4-dienones. These so-called ortho-quinols cyclodimerize via a remarkably selective bispericyclic Diels-Alder reaction. Whether or not the intervention of catalytic or dirigent proteins is involved during this final step of the biosynthesis of these natural products, this cyclodimerization of ortho-quinols can be chemically reproduced in the laboratory with the same strict level of site-specific regioselectivity and stereoselectivity. This unique yet unified process, which finds its rationale in the inherent chemical reactivity of those ortho-quinols, is illustrated herein by an efficient and bioinspired first chemical synthesis of one of the most structurally complex and synthetically challenging examples of such natural cyclodimers, the bisditerpenoid (+)-maytenone. |
| تدمد: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202103410 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::88e5e940aac8df36cc30c56dd110688d https://doi.org/10.1002/anie.202103410 |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....88e5e940aac8df36cc30c56dd110688d |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15213773 14337851 |
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| DOI: | 10.1002/anie.202103410 |