Synthesen in der Carotinoid‐Reihe. 6. Mitteilung. Synthese von Crocetindialdehyd und Lycopin
1956; Wiley; Volume: 39; Issue: 2 Linguagem: Inglês
10.1002/hlca.19560390217
ISSN1522-2675
AutoresO. Isler, Heike Gutmann, H. Lindlar, M. Montavon, R. Rüegg, G. Ryser, P. Zeller,
Tópico(s)Synthesis of Organic Compounds
ResumoAbstract A simple and efficient synthesis of lycopene is described based on stepwise lengthening of a symmetrical C 10 ‐dialdehyde as central component. This C 10 ‐dialdehyde is lengthened at both ends, first with vinyl ether and then with propenyl ether, leading to a C 20 ‐dialdehyde which is transformed into crocetin dialdehyde by partial hydrogenation of the central triple bond. By means of a new reaction devised by Wittig, crocetin dialdehyde is condensed at both ends with geranylidene‐triphenylphosphorane and lycopene is obtained according to the scheme C 10 + C 20 + C 10 = C 40 . This synthetic pigment is identical with pure natural lycopene isolated from tomato juice. The Wittig reaction also allows a new β‐carotene synthesis using the components cyclogeranylidene‐triphenylphosphorane and 8,8′‐dehydro‐crocetin dialdehyde.
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