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Diastereoselective Total Synthesis of (±)-Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System

  1. Tian-Wen Sun1,2,
  2. Dr. Wei-Wu Ren1,2,
  3. Dr. Qing Xiao1,2,
  4. Prof. Dr. Ye-Feng Tang3,
  5. Prof. Dr. Yan-Dong Zhang4,
  6. Yong Li1,2,
  7. Fan-Ke Meng1,2,
  8. Yi-Fan Liu1,2,
  9. Ming-Zhe Zhao1,2,
  10. Ling-Min Xu1,2,
  11. Prof. Dr. Jia-Hua Chen1,2,*,
  12. Prof. Dr. Zhen Yang1,2,*

Article first published online: 3 JUL 2012

DOI: 10.1002/asia.201200363

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 7, Issue 10, pages 2321–2333, October 2012

Additional Information

How to Cite

Sun, T.-W., Ren, W.-W., Xiao, Q., Tang, Y.-F., Zhang, Y.-D., Li, Y., Meng, F.-K., Liu, Y.-F., Zhao, M.-Z., Xu, L.-M., Chen, J.-H. and Yang, Z. (2012), Diastereoselective Total Synthesis of (±)-Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System. Chem. Asian J., 7: 2321–2333. doi: 10.1002/asia.201200363

Author Information

  1. 1

    Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS) and Peking-Tsinghua Center for Life Sciences at College of Chemistry of Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105

  2. 2

    Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen 518055 (China)

  3. 3

    The Comprehensive AIDS Research Center, School of Life Science and School of Medicine, Tsinghua University, Beijing 100084 (China)

  4. 4

    Department of Chemistry, Xiamen University, Xiamen 361005 (China)

*Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS) and Peking-Tsinghua Center for Life Sciences at College of Chemistry of Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105

Publication History

  1. Issue published online: 17 SEP 2012
  2. Article first published online: 3 JUL 2012
  3. Manuscript Received: 21 APR 2012

Funded by

  • National Basic Research Program. Grant Number: 2010CB833201
  • National Science and Technology Major Project “Development of Key Technology for the Combinatorial synthesis of Privileged Scaffolds”. Grant Number: 2009ZX09501-012
  • National Science Foundation of China. Grant Numbers: 20832003, 21072006, 21072111

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Keywords:

  • fused-ring systems;
  • natural products;
  • schindilactone A;
  • synthetic methods;
  • total synthesis

Abstract

First-generation synthetic strategies for the diastereoselective total synthesis of schindilactone A (1) are presented and methods for the synthesis of the ABC, FGH, and CDEF moieties are explored. We have established a method for the synthesis of the ABC moiety, which included both a Diels–Alder reaction and a ring-closing metathesis as the key steps. We have also developed a method for the synthesis of the FGH moiety, which involved the use of a Pauson–Khand reaction and a carbonylative annulation reaction as the key steps. Furthermore, we have achieved the construction of the central 7–8 bicyclic ring system by using a [3,3]-rearrangement as the key step. However, unfortunately, when this rearrangement reaction was applied to the construction of the more advanced CDEF moiety, the anticipated annulation reaction did not occur and the development of an alternative synthetic strategy would be required for the construction of this central core.

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