Total Synthesis of (+)-Brefeldin C, (+)-nor-Me Brefeldin A and (+)-4-epi-nor-Me Brefeldin A
| Autor: | Karine Aphecetche-Julienne, André Guingant, Sylvain Collet, Sylvie Archambaud, Frédéric Legrand, Michel Evain |
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| Přispěvatelé: | Service d'hématologie, Centre Hospitalier Régional Universitaire de Besançon (CHRU Besançon), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut des Matériaux Jean Rouxel (IMN), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Ecole Polytechnique de l'Université de Nantes (EPUN), Université de Nantes (UN)-Université de Nantes (UN) |
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry Organic Chemistry Absolute configuration Enantioselective synthesis Total synthesis Brefeldin A 010402 general chemistry 01 natural sciences Desymmetrization Chemical synthesis 0104 chemical sciences chemistry.chemical_compound chemistry [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci] Physical and Theoretical Chemistry Yamaguchi esterification Lactone |
| Zdroj: | European Journal of Organic Chemistry European Journal of Organic Chemistry, Wiley-VCH Verlag, 2010, pp.1364. ⟨10.1002/ejoc.200901233⟩ |
| ISSN: | 1099-0690 1434-193X |
| DOI: | 10.1002/ejoc.200901233 |
| Popis: | International audience; A total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed, Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the absolute configuration at C4 of BFC, a Suzuki-Miyaura cross-coupling reaction to create the C11-C12 bond and a Yamaguchi reaction to form the 13-membered lactone ring. |
| Databáze: | OpenAIRE |
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