The clinically important tricyclic prostaglandin D₂ metabolite (PGDM) methyl ester was synthesized in eight steps from a readily available known compound. The synthesis features Z-selective cross-metathesis to form the challenging Z β,γ-unsaturated ester, palladium-catalyzed carbonylative spirolactonization to build the oxaspirolactone moiety, and nickel-catalyzed Ueno–Stork-type dicarbofunctionalization to form two key C−C bonds and stereocenters.

中文翻译：

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三环前列腺素 D2 代谢物甲酯的催化简洁立体选择性全合成

临床上重要的三环前列腺素 D ₂代谢物 (PGDM) 甲酯是由一种容易获得的已知化合物通过八个步骤合成的。该合成的特点是Z-选择性交叉复分解形成具有挑战性的Z β,γ-不饱和酯，钯催化的羰基化螺内酯化形成氧杂螺内酯部分，以及镍催化的Ueno-Stork型二碳官能化形成两个关键的CC键和立构中心。