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
✍ Scribed by Alain Valla; Benoist Valla; Régis Le Guillou; Dominique Cartier; Laurent Dufossé; Roger Labia
- Publisher
- John Wiley and Sons
- Year
- 2007
- Tongue
- German
- Weight
- 112 KB
- Volume
- 90
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Since the C 15 b-end-group aldehyde 10 ((b-ionylidene)acetaldehyde), an excellent intermediate in the syntheses of retinoids, can be synthesized in many ways from b-ionone, and since the corresponding acyclic C 15 y-end-group aldehyde 5 can easily be synthesized from citral (1) (Scheme 3), we applied the C 15 þ C 5 route to the syntheses of g-retinal ((all-E)-8) (Scheme 3) and retinal ((all-E)-13) (Scheme 4), and therefore, by coupling (2 Â C 20 ! C 40 ), to the preparation of lycopene ( 14) and b-carotene (15) (Scheme 5). Our new syntheses of retinal ((all-E)-13) and g-retinal ((all-E)-8 use an extended aldol reaction with a C 6 building block that incorporates a C 5 unit after decarboxylation.