Full Paper

Efficient Total Synthesis of (S)-Dihydroresorcylide, a Bioactive Twelve-Membered Macrolide

  1. Li Zhang1,
  2. Wenquan Ma2,
  3. Lili Xu2,
  4. Fei Deng1,*,
  5. Yuewei Guo1,*

Article first published online: 1 MAR 2013

DOI: 10.1002/cjoc.201300016

Issue

Chinese Journal of Chemistry

Chinese Journal of Chemistry

Volume 31, Issue 3, pages 339–343, March, 2013

Additional Information

How to Cite

Zhang, L., Ma, W., Xu, L., Deng, F. and Guo, Y. (2013), Efficient Total Synthesis of (S)-Dihydroresorcylide, a Bioactive Twelve-Membered Macrolide. Chin. J. Chem., 31: 339–343. doi: 10.1002/cjoc.201300016

Author Information

  1. 1

    State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

  2. 2

    Biomedical Science Park of Weifang, Weifang National High-Tech Industrial Development Zone, Weifang, Shandong 261205, China

*State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China, Tel.: 0086-021-50805813; Fax: 0086-021-50805813

Publication History

  1. Issue published online: 18 MAR 2013
  2. Article first published online: 1 MAR 2013
  3. Manuscript Accepted: 1 FEB 2013
  4. Manuscript Received: 8 JAN 2013

Funded by

  • the Natural Science Foundation of China. Grant Number: 21021063, 81273430
  • the National Marine "863" Project. Grant Number: 2011AA09070102 and 2013AA092902
  • the SKLDR/SIMM Projects. Grant Number: SIMM1203ZZ-03

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Keywords:

  • dihydroresorcylide;
  • trans-resorcylide dimethyl ether;
  • ring-closing metathesis (RCM);
  • carbonylation;
  • total synthesis

Abstract

The efficient synthesis of (S)-dihydroresorcylide (1a) along with trans-resorcylide dimethyl ether (2b), was achieved in linear 9 steps from commercially available orcinol monohydrate (6) with esterification, carbonylation, and ring-closing metathesis (RCM) as the key steps in the synthetic sequence.

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