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Synlett 2001; 2001(11): 1759-1762
DOI: 10.1055/s-2001-18104
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Synthesis of all-E- and 9Z-Heteroaryl-retinoic Acid Applying Palladium Catalyzed Coupling Reaction of (Arylvinyl)tributyl Stannane with Vinyl Triflate

Akimori Wada* , Govindarajuru Babu, Sayaka Shimomoto, Masayoshi Ito
  • *Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan; E-mail: a-wada@kobepharma-u.ac.jp
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Publication Date:
29 October 2001 (online)

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Palladium catalyzed cross coupling reactions of (arylvinyl)tributyl stannanes with vinyl triflates resulted in the production of stereochemically pure trisubstituted E- and Z-olefins in very good yields. These olefins were transformed to the corresponding all-E- and 9Z-heteroaryl-retinoic acid analogs via Horner-Emmons reaction and subsequent basic hydrolysis in excellent yields.

retinoid X receptors - heteroaryl-retinoic acid - coupling reaction - vinyl triflate - (arylvinyl)tributyl stannane

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