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A Diastereoselective Route to trans-​2-​Aryl-​2,​3-​dihydrobenzofurans through Sequential Cross-​Metathesis​/Isomerization​/Allylboration Reactions: Synthesis of Bioactive Neolignans

Abstract : A new highly diastereoselective synthetic route to trans-2,3-dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross-metathesis/isomerization/allylboration sequence starting from 2-allyl-substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01138641
Contributor : Laurent Jonchère <>
Submitted on : Thursday, April 2, 2015 - 1:11:24 PM
Last modification on : Thursday, March 5, 2020 - 2:02:29 PM

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Rémy Hemelaere, François Carreaux, Bertrand Carboni. A Diastereoselective Route to trans-​2-​Aryl-​2,​3-​dihydrobenzofurans through Sequential Cross-​Metathesis​/Isomerization​/Allylboration Reactions: Synthesis of Bioactive Neolignans. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (11), pp.2470-2481. ⟨10.1002/ejoc.201500019⟩. ⟨hal-01138641⟩

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