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Stereocontrolled synthesis of retinoids functionalized at C-13 by suzuki coupling reactions

✍ 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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✦ 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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ChemInform Abstract: Stereocontrolled Sy
✍ Akimori Wada; Kouki Fukunaga; Masayoshi Ito πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 29 KB πŸ‘ 2 views

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