Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System
2018
Sun, Tian-Wen | Liu, Dong-Dong | Wang, Kuang-Yu | Tong, Bing-Qi | Xie, Jia-Xin | Jiang, Yan-Long | Li, Yong | Zhang, Bo | Liu, Yi-Fan | Wang, Yuan-Xian | Zhang, Jia-Jun | Chen, Jia-Hua | Yang, Zhen
The stereoselective construction of the CDEFGH ring system of lancifodilactone G is described. The key steps in this synthesis are (i) ring-closing metathesis for formation of the oxa-bridged eight-membered ring; (ii) an intramolecular Pauson–Khand reaction for construction of the sterically congested F ring; and (iii) sequential cross-metathesis, hydrogenation, and lactonization reactions for installation of the anomerically stabilized bis-spiro ketal fragment of lancifodilactone G.
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