Stereocontrolled Synthesis of 6-s-cis-and 6-s-trans-Locked 9 Z-Retinoids by Hydroxyl-Accelerated Stille Coupling of (Z)-Tri-n-Butylstannylbut-2-en-1-ol and Bicyclic …

B Domínguez, Y Pazos, AR de Lera

文献索引：Dominguez, Beatriz; Pazos, Yolanda; De Lera, Angel R. Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 5917 - 5925

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被引用次数: 37

摘要

Analogues of 9-cis-retinoic acid with locked 6-s-cis and 6-s-trans conformations have been stereoselectively synthesized using a Stille coupling reaction between bicyclic dienyl triflates (5 and 6, respectively) and (Z)-tributylstannylbut-2-en-1-ol (7) to stablish the Z geometry of the polyenic side chain. The mild conditions (25° C, 30 min) of this coupling stand in contrast to the reluctance of the isomeric (E)-tributylstannylbut-2-en-1-ol (18) to react with triflates 5 ...