Construction of the Pentacyclic Core of Yohimbine Alkaloids: A Chemoenzymatic Approach
Luyao Wu1, Zuming Lin1, Lili Zhu2
1Faculty of Chemical Engineering and Energy Technology, Shanghai Institute of Technology, Shanghai, P.R. China.
Abstract:
An enantiodivergent route was devised for accessing the two enantiomers of indolo[2,3-a]quinolizidine, which serve as a platform for the synthesis of Corynanthe alkaloids with dimorphic configurations at the C3 position. The cascade process, involving dipolar cycloaddition, N-O bond cleavage, and cyclization, minimizes the need for functional group elaboration. Subsequent alkylation, allylation, and ring-closing metathesis smoothly constructed the pentacyclic ring system embedded in yohimbine alkaloids. The inherent simplicity and efficiency of enzymatic kinetic resolution prove valuable for diverse structural derivatives.
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