New syntheses of retinal and its acyclic analog γ-retinal by an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation. A formal route to lycopene and β-carotene

Alain Valla 1 Benoist Valla Regis Le Guillou Dominique Cartier Laurent Dufossé 2 Roger Labia
1 Chimie et biologie des substances naturelles
2 LCSNSA - Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments
Abstract : Since the C15 β-end-group aldehyde (β-ionylidene)acetaldehyde, an excellent intermediate in the syntheses of retinoids, can be synthesized in many ways from β-ionone, and since the corresponding acyclic C15 ψ-end-group aldehyde can easily be synthesized from citral, the C15 + C5 route was applied to the syntheses of γ-retinal (I) and retinal (II), and therefore, by coupling (2 × C20 → C40), to the prepn. of lycopene and β-carotene. These new syntheses of retinal and γ-retinal use an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation. [on SciFinder(R)]
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http://hal.univ-reunion.fr/hal-01188165
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Submitted on : Friday, August 28, 2015 - 3:09:13 PM
Last modification on : Monday, September 2, 2019 - 9:43:11 AM

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Alain Valla, Benoist Valla, Regis Le Guillou, Dominique Cartier, Laurent Dufossé, et al.. New syntheses of retinal and its acyclic analog γ-retinal by an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation. A formal route to lycopene and β-carotene. Helvetica Chimica Acta, Wiley, 2007, 90 (3), pp.512--520. ⟨10.1002/hlca.200790053⟩. ⟨hal-01188165⟩

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