DOI: 10.1021/acs.joc.6c01318 ISSN: 0022-3263
Synthetic Studies toward (±)-Scandine Using Fe-Catalyzed Carbonyl Olefin Metathesis and Double α-Vinylation of Ketone
Xiao-Feng Zhu, Peng-Zhen Sheng, Jia-Wei Chen, Kun Wei, Yu-Rong YangAbstract
The complete carbon skeleton of a pentacyclic alkaloid, (±)-scandine, which lacks the B ring, was synthesized using a new approach. Major features include forming the C ring through Schindler’s FeCl3-catalyzed carbonyl-olefin metathesis and adding the characteristic divinyl substituents via Rawal’s recently developed protocol for α-vinylation of ketone.