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Neue Zugänge zu einigen aromatischen Retinoiden

 

作者: Milan Soukup,   Emil Broger,   Erich Widmer,  

 

期刊: Helvetica Chimica Acta  (WILEY Available online 1989)
卷期: Volume 72, issue 2  

页码: 370-376

 

ISSN:0018-019X

 

年代: 1989

 

DOI:10.1002/hlca.19890720224

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

New Approaches to Some Aromatic RetinoidsStarting from 2,3,5‐trimethylphenol (2), two pathways to ethyl (all‐E)‐9‐(4‐methoxy‐2,3,6‐trimethylphenyl)‐3,7‐dimethylnona‐2,4,6,8‐tetraenoate (1) and to some of its (Z)‐isomers have been developed. The first one is based on a Pd(O)‐catalyzed arylation of (Z)‐3‐methylpent‐2‐en‐4‐yn‐l‐ol (6) with 4‐bromo‐2,3,5‐trimethylanisol (5). The acetylenic C15−alcohol9was transformed into the corresponding acetylenic phosphonium salt10, which was catalytically hydrogenated to the olefinicWittigsalt.Wittigolefination led, then, to the (6Z, 8Z)‐ and (4Z, 6Z, 8Z)‐isomers,7and8, respectively. In a second approach,Friedel‐Craftsreaction of 3‐methylpent‐l‐en‐4‐yn‐3‐ol with the 2,3,5‐trimethylanisol gave a C15‐intermediate with a terminal CC bond in the side chain. After deprotonation and reaction with a C5aldehyd, the corresponding C20‐intermediate could be isolated in high yield. Finally, further conversion led pred

 

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