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Issue 10, 2015
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Synthesis of labile all-trans-7,8,7′,8′-bis-acetylenic carotenoids by bi-directional Horner–Wadsworth–Emmons condensation

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Abstract

A new stereoselective synthesis of the C40-bis-acetylenic carotenoids all-trans-(3R,3′R)-alloxanthin and all-trans-3,4,7,8,3′,4′,7′,8′-octadehydro-β,β-carotene, both compounds featuring a stereochemically labile C7–C10 enyne, based on a bi-directional Horner–Wadsworth–Emmons (HWE) reaction of a C15-phosphonate and a central C10-dialdehyde, is reported. The triene unit of the latter fragment was synthesized using the acyclic metathesis/dimerization reaction.

Graphical abstract: Synthesis of labile all-trans-7,8,7′,8′-bis-acetylenic carotenoids by bi-directional Horner–Wadsworth–Emmons condensation

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Publication details

The article was received on 08 Oct 2014, accepted on 13 Jan 2015 and first published on 13 Jan 2015


Article type: Paper
DOI: 10.1039/C4OB02144D
Citation: Org. Biomol. Chem., 2015,13, 3024-3031
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    Synthesis of labile all-trans-7,8,7′,8′-bis-acetylenic carotenoids by bi-directional Horner–Wadsworth–Emmons condensation

    B. Vaz, N. Fontán, M. Castiñeira, R. Álvarez and Á. R. de Lera, Org. Biomol. Chem., 2015, 13, 3024
    DOI: 10.1039/C4OB02144D

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