Xiaoyu Liu, Chengsen Tian, Xiaozhen Jiao, Xiaoyu Li, Hongguang Yang, Yangyang Yao and Ping Xie
Org. Biomol. Chem., 2016,14, 7715-7721
DOI:
10.1039/C6OB01346E,
Paper
A novel formal synthesis of Beraprost (1) is described. The tricyclic cyclopent[b]benzofuran core is efficiently prepared from (−)-Corey lactone diol in 12 steps with an overall yield of 37.4%. Key features of the strategy include a ring-closing metathesis reaction and aromatization to form the tricyclic cyclopenta[b]benzofuran framework, and selective halogenation/formylation to install the butyrate side-chain.
![Graphical abstract: A practical synthesis of chiral tricyclic cyclopenta[b]benzofuran, a key intermediate of Beraprost](/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=C6OB01346E "Graphical abstract")
