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Org Biomol Chem

Title:		"Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds"
Author(s):		Najera C; Foubelo F; Sansano JM; Yus M;
Address:		"Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain. cnajera@ua.es. Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain. cnajera@ua.es and Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain and Instituto de Sintesis Organica (ISO), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain"
Journal Title:		Org Biomol Chem
Year:		2020
Volume:		18
Issue:		7
Page Number:		1279 - 1336
DOI:		10.1039/c9ob02597a
ISSN/ISBN:		1477-0539 (Electronic) 1477-0520 (Linking)
Abstract:		"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, gamma-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, beta-amino acids, carboxylic acids, lactones, nitriles and alpha-amino nitriles have been considered as well"
Keywords:		Alcohols/chemical synthesis/chemistry Alkenes/chemical synthesis/chemistry Amines/chemical synthesis/chemistry Amino Acids/chemical synthesis/chemistry Biological Products/*chemical synthesis/chemistry Carboxylic Acids/chemical synthesis/chemistry Heteroc;
Notes:		"MedlineNajera, Carmen Foubelo, Francisco Sansano, Jose M Yus, Miguel eng Research Support, Non-U.S. Gov't Review England 2020/02/07 Org Biomol Chem. 2020 Feb 19; 18(7):1279-1336. doi: 10.1039/c9ob02597a"