Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C

Arindam Maity; Avishek Roy; Mrinal Kanti Das; Subhadip De; Malay Naskar; Alakesh Bisai

doi:10.1039/C9OB02752A

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Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C†

Arindam Maity,‡^a Avishek Roy,‡^a Mrinal Kanti Das,^a Subhadip De,^a Malay Naskar^a and Alakesh Bisai

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal - 462 066, Madhya Pradesh, India
E-mail: alakesh@iiserb.ac.in

^b Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia - 741 246, West Bengal, India
E-mail: alakesh@iiserkol.ac.in

Abstract

Efficient oxidative direct cyanations of 3-alkyl/aryl 2-oxindoles using Cyano-1,2-BenziodoXol-3(1H)-one (CBX) (2a) have been reported under ‘transition metal-free’ conditions to synthesize a wide variety of 3-cyano 3-alkyl/aryl 2-oxindoles sharing an all-carbon quaternary center under additive-free conditions. The application of this process is shown by the formal total synthesis of (±)-gliocladin C (11c) in a few steps.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB02752A
Article type: Paper
Submitted: 27 Dec 2019
Accepted: 03 Feb 2020
First published: 03 Feb 2020

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Org. Biomol. Chem., 2020,18, 1679-1684

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Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C

A. Maity, A. Roy, M. K. Das, S. De, M. Naskar and A. Bisai, Org. Biomol. Chem., 2020, 18, 1679 DOI: 10.1039/C9OB02752A

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Organic & Biomolecular Chemistry

Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C†

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Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C

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