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Synlett 1995; 1995(12): 1247-1248
DOI: 10.1055/s-1995-5257
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Stereocontrolled Functionalization at the C-9 of Retinal. Stereoselective Synthesis of 9-trans-9-Fluororetinal

Tetsuro Shinada, Noriko Sekiya, Nina Bojkova, Kazuo Yoshihara*
  • *Suntory Institute for Bioorganic Research, Wakayama-dai, Shimamoto-cho, Mishima-gun, Osaka 618, Japan, Fax 075-962-2115
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Publication Date:
31 December 2000 (online)

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A general functionalization at the C-9 of retinal with 9-trans-selectivity is described. A palladium-catalyzed cross-coupling reaction of 6 and 7 afforded 6E-8, which was elaborated to 9-trans-9-fluororetinal via the stereo- and regioselective isomerization.

retinal - cross-coupling - Horner-Emmons reaction - conjugate addition - isomerization

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