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New Paper on Nat. Commun. has been Published Online
Our new paper regarding Asymmetric Total Synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] Cycloaddition has been published online in Nature Communications, 2014, 5:5707. This achievement was completed by Rong Long and Jun Huang with their coworkers Wenbin Shao, Song Liu, Yu Lan instructed by Dr. Jianxian Gong and Prof. Zhen Yang.
The development of efficient reactions for the one-pot construction of bicyclic ring systems bearing two quaternary carbon centres at their bridgehead positions represents a significant challenge to synthetic chemistry. The development of new methods capable of overcoming this challenge is highly desirable, because this motif can be found in a wide range of natural products with significant biological activities. Herein, we report an efficient [3+2] cycloaddition reaction between an enal and an alleno rhodium species, which was generated in situ from the corresponding enynol via a retro metal-propargylation reaction, to give [3.3.0] and [3.4.0] bicyclic systems bearing two quaternary atoms at their bridgehead positions. The developed chemistry has been successfully applied to the asymmetric total synthesis of natural product (−)-lingzhiol for the first time in 17 steps.
