Efficient Synthesis of 11-cis-Retinoids

✍ Scribed by Babak Borhan; María L. Souto; Joann M. Um; Bishan Zhou; Koji Nakanishi

• Book ID: 101303992
• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 100 KB
• Volume: 5
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/(sici)1521-3765(19990401)5:4<1172::aid-chem1172>3.0.co;2-q

✦ Synopsis

The light sensitivity and unstable nature of 11-cis-retinoids makes them ideal visual chromophores in nature. The synthesis of 11-cis-retinal analogues is of paramount importance in bioorganic studies of rhodopsin, the photoreceptor of the visual transduction pathway, but the instability of 11-cis-retinoids complicates their synthesis and there is no general synthetic route. Common strategies to the cis geometry have failed in the case of 11-cis-retinoids, and most often low yields and complex isomeric mixtures are obtained. Herein we report an efficient, general, and mild preparation of 11-cis-retinoids by semi-hydrogenation of 11-yne-retinoid precursors with Cu/Ag-activated zinc dust.