Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds
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Título: | Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds |
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Autor/es: | Nájera, Carmen | Foubelo, Francisco | Sansano, Jose M. | Yus, Miguel |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Stereodivergent routes | Organic synthesis | Marine natural products | Lactones | Heterocycles | Unnatural compounds |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 2020 |
Editor: | Royal Society of Chemistry |
Cita bibliográfica: | Organic & Biomolecular Chemistry. 2020, 18: 1279-1336. doi:10.1039/C9OB02597A |
Resumen: | Enantio- and diastereodivergent routes to marine-origin natural products with different sizes of cyclic ethers and lactones have been used in order to assign stereochemical features. Kainoid amino acids such as isodomoic acids have been synthesized using diastereodivergent routes. The bis(indole) alkaloid dragmacidin F has been prepared by enantiodivergent strategies as well as furanoterpenes and the tetracyclic agelastatin A. Natural products containing five-membered lactones like quercus lactones, muricatacins, goniofufuranones, methylenolactocins and frenolicin B have been synthesized using stereodivergent routes. Macrolides are very abundant lactones and have been mainly prepared from the corresponding seco-acids by lactonization, such as lasiodiplodin, zaeralanes, macrosphelides and haloprins, or by ring-closing metathesis, such as aspercyclides, microcarpalides, macrolides FD-891 and 892, and tetradic-5-en-9-olides. Other natural products including cyclic ethers (such as sesamin, asarinin, acetogenins, centrolobines and nabilones), alcohols (such as sulcatol), esters (such as methyl jasmonates), polycyclic precursors of fredericamycin, amino alcohols (such as ambroxol and sphingosines), isoprostanes, isofurans, polyketide precursors of anachelins, brevicomins, gummiferol, shikimic acid and the related compounds, and the pheromone disparlure have been synthesized stereodivergently. Heterocyclic systems such as epoxides, theobroxides and bromoxones, oxetan-3-ones, 5- to 8-membered cyclic ethers, azetidones, γ-lactams, oxazolidinones, bis(oxazolines), dihydropyridoisoindolines and octahydroisoquinolines have been prepared following stereodivergent routes. Stereodivergent routes to unnatural compounds such as alkenes, dienes, allenes, cyclopropanes, alcohols, aldols, amines, amino alcohols, β-amino acids, carboxylic acids, lactones, nitriles and α-amino nitriles have been considered as well. |
Patrocinador/es: | We thank the Spanish Ministerio de Economía, Industria y Competitividad, Gobierno de España, Agencia Estatal de Investigación (AEI) and European Regional Development Fund (FEDER, EU) (projects CTQ2016-76782-P, CTQ2016-81797-REDC, and CTQ2017-85093-P), the Generalitat Valenciana (PROMETEOII/2014/017) and the Universidad de Alicante for financial support. |
URI: | http://hdl.handle.net/10045/102987 |
ISSN: | 1477-0520 (Print) | 1477-0539 (Online) |
DOI: | 10.1039/C9OB02597A |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © The Royal Society of Chemistry 2020 |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1039/C9OB02597A |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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2020_Najera_etal_OrgBiomolChem_II_final.pdf | Versión final (acceso restringido) | 6,64 MB | Adobe PDF | Abrir Solicitar una copia |
2020_Najera_etal_OrgBiomolChem_II_preprint.pdf | Preprint (acceso abierto) | 5,28 MB | Adobe PDF | Abrir Vista previa |
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