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

Chandrasekhar, Srivari

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

Posted on 2020-10-20 - 17:20

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.

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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. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c03155

https://doi.org/10.1021/acs.orglett.0c03155

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