TY - DATA T1 - An Accelerated Intermolecular Rauhut–Currier Reaction Enables the Total Synthesis of (−)-Flueggenine C PY - 2017/04/24 AU - Sangbin Jeon AU - Sunkyu Han UR - https://acs.figshare.com/articles/journal_contribution/An_Accelerated_Intermolecular_Rauhut_Currier_Reaction_Enables_the_Total_Synthesis_of_-Flueggenine_C/4928690 DO - 10.1021/jacs.7b02751.s001 L4 - https://ndownloader.figshare.com/files/8291264 KW - securinega KW - flueggenine KW - RC reaction KW - Rauhut KW - monomeric KW - synthesis KW - dimeric N2 - The first total synthesis of dimeric securinega alkaloid (−)-flueggenine C is completed via an accelerated intermolecular Rauhut–Currier (RC) reaction. Despite the numerous reports on the total synthesis of monomeric securinegas, the synthesis of dimeric securinegas whose monomeric units are connected by a putative enzymatic RC reaction has not been reported to date. We have found that installation of a nucleophilic functional group at the γ-position of an enone greatly accelerates the rate of the diastereoselective intermolecular RC reaction. This discovery enabled an efficient and selective formation of the dimeric intermediate which was further transformed to (−)-flueggenine C. ER -