Polycyclic Indolines by an Acid‐Mediated Intramolecular Dearomative Strategy: Reversing Indole Reactivity in the Pictet‐Spengler‐Type Reaction. Issue 21 (13th September 2018)

• Record Type: Journal Article
• Authors: Ciccolini, Cecilia; Mari, Michele; Lucarini, Simone; Mantellini, Fabio; Piersanti, Giovanni; Favi, Gianfranco
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 21(2018)
• Page Start: 4060
• Page End: 4067
• Publication Date: 2018-09-13
• Subjects: Indoline -- Indolium -- Dearomatization -- Pictet-Spengler -- Metal-free; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201800981
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :