Biology-Oriented Synthesis of Decahydro-4,8-epoxyazulene ScaffoldsC.M. thanks the FCI for a Liebig Fellowship and the Deutsche Forschungsgemeinschaft (DFG) for support through the Cluster of Excellence RESOLV (‘Ruhr Explores Solvation’, EXC 1069). This research was supported by the European Research Council under the Seventh Framework Programme of the European Union (FP7/2007–2013; ERC Grant 268309 to H.W.) and by the Max Planck Society.
Received: 13 June 2017
Accepted after revision: 28 July 2017
23 August 2017 (eFirst)
Dedicated to Victor Snieckus on the occasion of his 80th birthday
Guided by the principle of biology-oriented synthesis, a collection of compounds with decahydro-4,8-epoxyazulene scaffold occurring in bioactive natural products was synthesized by the rhodium(II)-catalyzed 1,3-dipolar cycloaddition reaction of pentafulvenes and carbonyl ylides. The products can be obtained in moderate to high yields, with moderate enantioselectivity and excellent diastereoselectivity and regioselectivity.