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).
Highlights
Complex polycyclic scaffolds are widely present in biologically important alkaloid natural products
Partly due to the linear nature of the alkyne unit, controlling the enantioselectivity of such dearomatization reactions is challenging. This is illustrated by the limited number of enantioselective dearomatization reactions of alkyne-tethered indoles reported in the literature.[5]
We report the successful realization of a Ag(I)-catalyzed enantioselective dearomatizing[6] cascade sequence for the rapid construction of the akuammiline alkaloid core scaffold 9 via ynone-tethered indoles 7 (Scheme 1B)
Summary
Complex polycyclic scaffolds are widely present in biologically important alkaloid natural products.
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