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.