P-14 9Z-レチノイン酸の効率的合成とアナログ合成への応用(ポスター発表の部)

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9Z-Retinoic acid 1 and its synthetic analogues bind to RXRs (Retinoid X receptors) and regulate various biological functions such as cell differentiation, proliferation, and control of embryonic development. Therefore, the development of an efficient synthetic route of 1 and its synthetic analogues is desirable. In this presentation, we will demonstrate an efficient, rapid synthesis of 1 that includes Stille coupling reaction of stannanyl ester 4, having an electron-withdrawing group. as a key reaction. Advantages of our method are as follows; 1) Stannanyl ester 4 can be prepared from commercially available alcohol 6 in only three steps with in a large scale procedure. 2) The isomerization of the Z-double bond does not occur in the reaction. 3) Our originally developed stannanyl ester 4 can serve as a practical building block in convergent syntheses leading to useful analogues. Although Stille coupling reaction using organostannane with electron-withdrawing group has usually suffered from its unreactivity and homo-coupling, the use of cesium fluoride (CsF) as an additive caused not only the enhancement of the reaction rate but also the avoidance of the isomerization of Z-double bond. This Stille coupling reaction enabled us to accomplish the total synthesis of 1 in three steps from the aldehyde 2 in 63.0% overall yield or in five steps from the alcohol 6 in 62.7% overall yield. In conclusion, we developed a rapid synthesis of 9Z-retinoic acid 1, and a highly efficient, convergent synthetic route of its analogues by cesium fluoride promoted Stille coupling reaction using common stannyl ester 4.
天然有機化合物討論会の論文
2008-09-01

P-14 9Z-レチノイン酸の効率的合成とアナログ合成への応用(ポスター発表の部)

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