Total Synthesis of 5-(3-Indolyl)oxazole Natural Product via Gold-Catalyzed Intermolecular Alkyne Oxidation

Yundong Wu, Sha Peng, Yuejun Ouyang, Pengcheng Qian, Weimin He, Jiannan Xiang
2012 Huaxue xuebao  
The recent development of new gold(I) catalytic methods has opened the door to the total synthesis of natural products and bioactive complex molecules. We describe a convenient, straightforward, efficient and environmentally benign protocol to synthesize the 5-(3-indolyl)oxazole. The new synthetic route was finished in five steps including iodization, N-Boc protection, Sonogashira cross-coupling, gold catalyzed reaction, deprotection using indole as the starting material. The key step was
more » ... tion of α-oxo carbene via gold-catalyzed intermolecular oxidation of alkynes (2).
doi:10.6023/a1111101 fatcat:bcsduufpujcbphevsxqawik34i