Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

An Accelerated Intermolecular Rauhut–Currier Reaction Enables the Total Synthesis of (−)-Flueggenine C

An Accelerated Intermolecular Rauhut–Currier Reaction Enables the Total Synthesis of (−)-Flueggenine C
Sangbin Jeon, Sunkyu Han
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b02751

DOI: 10.1021/jacs.7b02751

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