Diastereoselective Synthesis of Cyclopentanoids: Applications to the Construction of the ABCD Tetracyclic Core of Retigeranic Acid A

A concise and efficient approach for the construction of the tetracyclic carbon skeleton of retigeranic acid A is described. The key transformations include a novel Rh-catalyzed [3+2] cycloaddition of enyol to afford cyclopentanoid E, bearing two contiguous quaternary stereocenters at the bridgehead positions, and an intramolecular Pauson-Khand reaction to construct the advanced tetracyclic core structure of retigeranic acid A.NSF of China [21372016, 21402002]; 863 Program [2013AA092903]; 973 Program [2012CB722602]; NSFC-Shandong Joint Fund for Marine Science Research Center [U1406402]; Shenzhen Basic Research Program [JCYJ20130329180217059, ZDSYS20140509094114168]SCI(E)EIPubMedARTICLElanyu@cqu.edu.cn; gongjx@pku.edu.cn; zyang@pku.edu.cn3612596-126002