[4+2]/HyBRedOx Approach toC-Naphthyl Glycosides: Failure in the Projuglone Series and Reinvestigation of the HyBRedOx Sequence

Autor: Nguyen Quang Vu, André Guingant, Sylvain Collet, Arnaud Martel, Lucie Maingot, Gilles Dujardin
Přispěvatelé: Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), 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)
Rok vydání: 2009
Předmět:
Zdroj: European Journal of Organic Chemistry
European Journal of Organic Chemistry, Wiley-VCH Verlag, 2009, pp.412-422. ⟨10.1002/ejoc.200800655⟩
ISSN: 1099-0690
1434-193X
DOI: 10.1002/ejoc.200800655
Popis: International audience; C-Naphthyl glycosides displaying a 1,5-difunctionality on the naphthalene ring that can undergo oxidation to bromonaphthoquinone are key intermediates in the synthesis of natural C-aryl glycoside analogues. In this area, sugar-modified derivatives are of specific interest, but their synthesis is challenging. The de novo access to such compounds has been investigated through a [4+2] heterocycloaddition route, previously validated in a model series. For this purpose, two new dienophiles, conveniently protected at the phenolic positions, were synthesized. From an extensive study of their reactivity towards a range of 4-hetero-substituted (''prosugar'') heterodienes, the expected heteroadducts were stereoselectively obtained in acceptable yields. Application of the hydroboration/reduction/oxidation sequence did not afford the target C-glycosides from the reduced adducts. The negative effect of the conformational bias of the substrate on this tandem reaction is discussed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Databáze: OpenAIRE
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