Communication

Enantioselective and Collective Syntheses of Xanthanolides Involving a Controllable Dyotropic Rearrangement of cis-β-Lactones†

  1. Dr. Weiwu Ren1,
  2. Yichao Bian1,
  3. Ziyang Zhang1,
  4. Dr. Hai Shang1,
  5. Pengtao Zhang1,
  6. Yuejie Chen1,
  7. Prof. Dr. Zhen Yang2,*,
  8. Dr. Tuoping Luo3,*,
  9. Prof. Dr. Yefeng Tang1,*

Article first published online: 4 JUN 2012

DOI: 10.1002/anie.201202643

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 28, pages 6984–6988, July 9, 2012

Additional Information

How to Cite

Ren, W., Bian, Y., Zhang, Z., Shang, H., Zhang, P., Chen, Y., Yang, Z., Luo, T. and Tang, Y. (2012), Enantioselective and Collective Syntheses of Xanthanolides Involving a Controllable Dyotropic Rearrangement of cis-β-Lactones . Angew. Chem. Int. Ed., 51: 6984–6988. doi: 10.1002/anie.201202643

Author Information

  1. 1

    The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)

  2. 2

    Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871 (China)

  3. 3

    H3 Biomedicine Inc., 300 Technology Square, Cambridge, MA 02139 (USA)

*Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871 (China)

  1. †

    We acknowledge the financial support from the National Science of Foundation of China (20832003), China’s 985 project (411307141), and New Teachers’ Fund for Doctor Stations, Ministry of Education (20110002120011) to Y.T. T.L. is grateful to Prof. Stuart L. Schreiber (Harvard University) for the inspiring education.

Publication History

  1. Issue published online: 4 JUL 2012
  2. Article first published online: 4 JUN 2012
  3. Manuscript Received: 5 APR 2012

Funded by

  • National Science of Foundation of China. Grant Number: 20832003
  • China’s 985 project. Grant Number: 411307141
  • New Teachers’ Fund for Doctor Stations
  • Ministry of Education. Grant Number: 20110002120011

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Keywords:

  • dyotropic rearrangement;
  • lactones;
  • rearrangement;
  • total synthesis;
  • xanthanolides
Thumbnail image of graphical abstract

Let's swap: A scalable, atom-economic, enantio-, and diastereoselective synthetic route to trisubstituted γ-butyrolactones based on a Wagner–Meerwein-type dyotropic rearrangement of cis-β-lactones is described (see scheme). This methodology was applied in efficient and protecting-group-free formal syntheses and total syntheses of various xanthanolide natural products.

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