本論文的研究主題是將「環閉合置換反應（ring-closing metathesis , RCM）後產生之烯烴進行具位置選擇性衍生化的方法」，藉由鈀金屬催化甲酸還原反應(palladium-catalyzed formate reduction)來達成此目的。我們使用含氧原子的七圓雜環化合物 4 為模型，以改變甲酸還原反應中磷配位基的方式，找出適用含氧七圓雜環產生環外烯的最佳條件。 為了探討此系統對於有機合成上得實用性，我們以Cossy教授合成天然物Zoapatanol時，合成路徑中的中間物化合物 C5為目標產物。Zoapatanol的主體架構為含有兩個掌性中心的含氧七圓雜環，而第一個掌性中心的建構是利用Sharpless進行不對稱氧化來得到，第二個掌性中心則是以Felkin-Anh model來建構出第二個掌性中心。 The method for regioselective palladium-catalyzed formate reduction of allylic acetates formed by ring closing metathesis was developed. We used ((E)-2,5,6,7-tetrahydro-7-methyl-7-phenyloxepin-3-yl)methyl acetate 4 as the model compound, and found an optimized condition for the formate reduction by screening several ligand. In order to apply this methodology to organic synthesis , We planned to synthesize compound C5 , that was the key synthetic intermediate in Cossy’s synthesis to product Zoapatanol . Zoapatanol contains a seven membered oxygen-heterocycle with two chiral centers. The first chiral center was prepared utilizing the Sharpless asymmetric oxidation, and the second chiral center was built by Grignard reaction whose stereochemistry assume to follow the Felkin-Anh model.
