Abstract
Natural products offer powerful bioactive compounds that serve as leads for new-age
therapeutics. Alkaloid natural products containing C3-alkylated indolines embed an all-carbon
quarternary ring system that is we documented as a privileged scaffold in natural product chemistry
and drug design. Inspired by the Nocardioazines A and B that are prenylated, bioactive
pyrroloindoline natural products, isolated from Nocardiopsis, we envisioned that Indoline-fused-
3,4-pyrroles offer a new scaffold to explore their biological importance. A biomimetic pathway
that provides access to 6-5-6-5 and 6-5-7-5 C3-alkylated indoline-3,4-pyrrole fusion products that
are new to heterocyclic chemistry is described. The reactivity profile presented in the form of a
cascade process, executed smoothly as a single-pot reaction is unprecedented for three reasons,
with isolated yields being high to excellent. The entire process works without any protecting
groups while functionalizing two aromatic rings and the process offers indolines tethered with
pyrrole at the C2 position with high regioselectivity. In summary, simple alkynes are transformed
dramatically into complex natural-product-like cores smoothly, with broad substrate scope
Supplementary materials
Title
SI-1
Description
Experimental Procedure, Compound Characterization Data
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Title
SI-2
Description
NMR Spectras
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