Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade
James A Rossi-Ashton1, Aimee K Clarke1, Richard J K Taylor1
1Department of Chemistry , University of York , York , YO10 5DD , U.K.
Abstract:
The polycyclic core of the akuammiline alkaloids can be synthesized from simple tryptamine and tryptophol derivatives via a Ag(I)-catalyzed enantioselective dearomative cyclization cascade sequence. The complex tetracyclic scaffolds are prepared via a rapid, versatile, three-step modular synthesis from simple commercially available indole derivatives in high yields and enantiomeric excess (up to 99% yield and >99% ee).
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