Communication

Total Synthesis of Polyene Natural Product Dihydroxerulin by Mild Organocatalyzed Dehydrogenation of Alcohols

  1. Dr. Hexin Xie1,
  2. Dr. Shilei Zhang1,*,
  3. Prof. Dr. Hao Li2,
  4. Xinshuai Zhang1,
  5. Sihan Zhao1,
  6. Zian Xu2,
  7. Xixi Song1,
  8. Prof. Dr. Xinhong Yu2,*,
  9. Prof. Dr. Wei Wang1,2,*

Article first published online: 25 JAN 2012

DOI: 10.1002/chem.201103325

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 8, pages 2230–2234, February 20, 2012

Additional Information

How to Cite

Xie, H., Zhang, S., Li, H., Zhang, X., Zhao, S., Xu, Z., Song, X., Yu, X. and Wang, W. (2012), Total Synthesis of Polyene Natural Product Dihydroxerulin by Mild Organocatalyzed Dehydrogenation of Alcohols. Chem. Eur. J., 18: 2230–2234. doi: 10.1002/chem.201103325

Author Information

  1. 1

    Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609

  2. 2

    School of Pharmacy, East University of Science and Technology, Shanghai 200237 (P. R. China), Fax: (+86) 21-6425-2604

*Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA), Fax: (+1) 505-277-2609

Publication History

  1. Issue published online: 10 FEB 2012
  2. Article first published online: 25 JAN 2012
  3. Manuscript Received: 21 OCT 2011

Funded by

  • National Science Foundation. Grant Number: CHE-1057569
  • China 111 Project. Grant Number: B07023
  • East China University of Science & Technology
  • National Science Foundation of China. Grant Number: 20972051
  • Shanghai Pujiang Program. Grant Number: 11PJ1411900
  • Science and Technology Commission of Shanghai Municipality. Grant Numbers: 08430703900, 08431901800

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Keywords:

  • dehydrogenation;
  • dihydroxerulin;
  • enals;
  • organocatalysis;
  • oxidative enamine catalysis;
  • polyenes
Thumbnail image of graphical abstract

Polyene synthesis: An efficient approach to the total synthesis of polyene natural product dihydroxrulin (1) is described. A novel, mild, direct organocatalytic IBX-mediated dehydrogenation process of simple alcohols to enals has been developed, which serves as a key step in the synthesis (see scheme).

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