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Al-Catalyzed Facile Construction of Quaternary C[BOND]C Bonds by the Allylic Substitution of Tertiary Alcohols: A Concise and Formal Synthesis of (±)-Mersicarpine

  1. Xue Zhong1,2,
  2. You Li1,
  3. Dr. Fu-She Han1,3,*

Article first published online: 28 JUN 2012

DOI: 10.1002/chem.201201344

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 32, pages 9784–9788, August 6, 2012

Additional Information

How to Cite

Zhong, X., Li, Y. and Han, F.-S. (2012), Al-Catalyzed Facile Construction of Quaternary C[BOND]C Bonds by the Allylic Substitution of Tertiary Alcohols: A Concise and Formal Synthesis of (±)-Mersicarpine. Chem. Eur. J., 18: 9784–9788. doi: 10.1002/chem.201201344

Author Information

  1. 1

    Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022 (China), Tel: (+86) 431-8526-2936

  2. 2

    Graduate School of Chinese Academy of Sciences, Beijing, 100864 (P.R. China)

  3. 3

    The State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, 200032 (P.R. China)

*Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022 (China), Tel: (+86) 431-8526-2936

Publication History

  1. Issue published online: 28 JUL 2012
  2. Article first published online: 28 JUN 2012
  3. Manuscript Received: 20 APR 2012

Funded by

  • Hundred Talent Program
  • State Key Laboratory of Bio-organic and Natural Products Chemistry. Grant Number: 09182

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Keywords:

  • allylic compounds;
  • aluminum;
  • Friedel–Crafts reaction;
  • Grignard reaction;
  • mersicarpine;
  • quaternary carbon;
  • Wolff–Kishner reduction
Thumbnail image of graphical abstract

In close quarters: A concise, high-yielding, and more sustainable route for the synthesis of (±)-mersicarpine in nine linear steps from commercially available indole and succinic anhydride is presented (see scheme). It is also demonstrated that the novel protocol can be commonly used for the rapid and flexible construction of a diverse class of mersicarpine analogues.

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