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Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
Published on: November 11, 2008
An Accelerated Intermolecular Rauhut-Currier Reaction Enables the Total Synthesis of (-)-Flueggenine C
Sangbin Jeon1,2, Sunkyu Han1,2
1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , Daejeon 34141, Korea.
Abstract:
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.
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