94.Diastereoselective Synthesis of Cyclopentanoids: Applications to the Construction of the ABCD Tetracyclic Core of Retigeranic Acid A [Inside Back Cover]

Junlin Zhang, Xiao Wang, Shuang Li, Dian Li, Song Liu, Prof. Dr. Yu Lan*, Dr. Jianxian Gong*, Prof. Dr. Zhen Yang*

Chem. Eur. J. 2015, 21, 1256.

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.

 

2015_21_36c

Abstract