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- W2009871104 abstract "Die Darstellung von Vitamin-A-Derivaten, die in 13-, 9- und 11-Stellung Methoxysubstituenten tragen, wird beschrieben. Hierbei stellen der C4-Baustein 21 und das von ihm abgeleitete Phosphonat 22 Schlüsselsubstanzen dar. Für 21 werden mehrere Herstellungsweisen vorgestellt und miteinander verglichen. Durch Wittig-Horner-Reaktion von 22 mit dem β-C15-Aldehyd 24 wird der 13-Methoxyretinsäureester 25 erhalten, der zu 13-Desmethyl-13-methoxyretinal (26) reduziert wird. Ausgehend von β-Cyclocitral (27) wird durch Reformatzky-Reaktion mit 21 das Methoxylacton 31 hergestellt, das sich durch basische Ringöffnung stereospezifisch in die Carbonsäure 33 überführen läßt. Deren Reduktions-produkt, der Aldehyd 34, läßt sich mit verschiedenen Phosphonaten (36, 37, 22) verknüpfen, wodurch die Methoxyretinoide 38–40 zugänglich werden. Der β-C12-Aldehyd 41 und β-Ionon (46) dienen als Ausgangsmaterialien für 9,13-Bis(desmethyl)-11-methoxyretinal (45) und 13-Desmethyl-11-methoxyretinal (50); im ersten Fall bildet die Wittig-Horner-Reaktion zwischen 41 und 22, im zweiten die Reformatzky-Reaktion von 46 mit 21 den entscheidenden Kettenverlängerungsschritt. Retinoids, XI. — Preparation of 13-, 9-, and 11-Methoxyretinoids The synthesis of vitamin A derivatives carrying methoxy substituents in positions 13, 9, and 11 is described. The C4-building block 21 and the phosphonate derived from it, 22, serve as key intermediates for these preparations. Several routes leading to 21 are described and compared with each other. Wittig-Horner reaction between 22 and the β-C15-aldehyde 24 provides the 13-methoxyretinoate 25 which is reduced to 13-demethyl-13-methoxyretinal (26). Starting from β-cyclocitral (27), Reformatzky reaction with 21 furnishes the methoxy lactone 31 which is opened stereospecifically to give the carboxylic acid 33 by base treatment. The reduction product of 33, aldehyde 34, is coupled with various phosphonates (36, 37, 22) thus opening up routes to the methoxyretinals 38–40. The β-C12-aldehyde 41 and β-ionone (46) serve as substrates for 9,13-bis(demethyl)-11-methoxyretinal (45) and 13-demethyl-13-methoxyretinal (50); in the former case Wittig-Horner reaction between 41 and 22 serves as the decisive chain-elongation step, whereas Reformatzky coupling between 46 and 21 is used for this purpose in the latter." @default.
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- W2009871104 title "Retinoide, XI Die Darstellung von 13-, 9- und 11-Methoxyretinoiden" @default.
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- W2009871104 doi "https://doi.org/10.1002/jlac.198819880714" @default.
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