Cation Triggered Domino Aza-Piancatelli Rearrangement/Friedel–Crafts Alkylation of Indole-Tethered Furfuyl Alcohols to Access Cycloocta[b]indole Core of Alkaloids

Vonteddu, Nagarjuna Reddy ; Solanke, Pooja R. ; Nayani, Kiranmai ; Chandrasekhar, Srivari (2020) Cation Triggered Domino Aza-Piancatelli Rearrangement/Friedel–Crafts Alkylation of Indole-Tethered Furfuyl Alcohols to Access Cycloocta[b]indole Core of Alkaloids Organic Letters, 22 (21). pp. 8555-8560. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.0c03155

Related URL: http://dx.doi.org/10.1021/acs.orglett.0c03155

Abstract

A domino approach to bridged cycloocta[b]indolone through a cascade of aza-Piancatelli rearrangement/Friedel–Crafts alkylation is developed. This transformation has been realized by reaction of an indole-tethered 2-furylcarbinol and substituted aniline in the presence of a Lewis acid to initiate aza-Piancatelli rearrangement followed by an in situ intramolecular Friedel–Crafts alkylation to access bridged tetracyclic frameworks in one pot.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:131272
Deposited On:06 Dec 2022 08:45
Last Modified:06 Dec 2022 08:45

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