Utilizing the pKa Concept to Address Unfavorable Equilibrium Reactions in the Total Synthesis of Palau’amine
Eisaku Ohashi,
Kohei Takeuchi,
Keiji Tanino
et al.
Abstract:Herein, we introduce the pKa concept as a strategy for proceeding with unfavorable reactions in the total synthesis of palau’amine. The cascade reaction aimed at constructing palau’amine’s ABDE tetracyclic ring core initially encountered poor reproducibility due to an unfavorable equilibrium reaction. However, the addition of 1.0 equivalent of AcOH enabled the progression of the unfavorable equilibrium reaction. In the second-generation synthesis, the improved cascade reaction to construct CDE ring core also i… Show more
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