Stereocontrolled synthesis of retinoids functionalized at C-13 by suzuki coupling reactions
β Scribed by Rosana Alvarez; Beatriz Iglesias; Angel R. de Lera
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 923 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
The retinal analogues ( 13Z)-13-bromo-13-desmethylretinal (3) and ( 13E)-20,20,20-trifluororetinal (4) have been efficiently synthesized using the palladium-catalyzed cross-coupling of boronic acid 8 and electrophiles 9 and 10, respectively. For the first analogue, the coupling of 8 and the gem-dibromide 9 took place with high stereoselectivity.
The configuration of the C13-Cl4 double bond in 4 relied on the stereoselective preparation and coupling of alkenyltriflate Z-10 from P-ketoester 15.
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