Polycyclic Indolines by an Acid‐Mediated Intramolecular Dearomative Strategy: Reversing Indole Reactivity in the Pictet‐Spengler‐Type Reaction | Zendy

Ciccolini Cecilia | Zendy; Mari Michele | Zendy; Lucarini Simone | Zendy; Mantellini Fabio | Zendy; Piersanti Giovanni | Zendy; Favi Gianfranco | Zendy

Premium

Polycyclic Indolines by an Acid‐Mediated Intramolecular Dearomative Strategy: Reversing Indole Reactivity in the Pictet‐Spengler‐Type Reaction

Author(s) -

Ciccolini Cecilia,

Mari Michele,

Lucarini Simone,

Mantellini Fabio,

Piersanti Giovanni,

Favi Gianfranco

Publication year - 2018

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201800981

Subject(s) - chemistry , tryptamine , indole test , indoline , intramolecular force , reactivity (psychology) , pictet–spengler reaction , tryptophan , combinatorial chemistry , stereochemistry , organic chemistry , amino acid , medicine , biochemistry , alternative medicine , pathology

Indoline‐fused polycycles were synthesized through a TFA‐promoted intramolecular dearomative cyclization of indole‐tethered pyrroles. Mechanistically, the strategic carbon‐carbon bond formation is hypothesized to proceed via a Pictet‐Spengler‐type reaction wherein a reversal of conventional indole reactivity of tryptamine derivatives occurs. The synthetic versatility of this operationally simple, atom‐economic approach is demonstrated in the preparation of the pyrido[1,2‐ a :3,4‐ b′ ]diindole core of natural product homofascaplysin C.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research