Asymmetric Total Synthesis of Antibiotic Elansolid A

Research output: Contribution to journalArticleResearchpeer review

Authors

  • Liang Liang Wang
  • Qi Yu
  • Wenjing Zhang
  • Shuai Yang
  • Lin Peng
  • Liang Zhang
  • Xiao Nian Li
  • Fabien Gagosz
  • Andreas Kirschning

Research Organisations

External Research Organisations

  • Kunming Institute of Botany Chinese Academy of Sciences
  • Shaoyang University
  • Zhengzhou University
  • University of Ottawa
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Details

Original languageEnglish
Pages (from-to)6871-6881
Number of pages11
JournalJournal of the American Chemical Society
Volume144
Issue number15
Early online date12 Apr 2022
Publication statusPublished - 20 Apr 2022

Abstract

Elansolid A is a structurally complex polyketide macrolactone natural product that exhibits promising antibacterial properties. Its challenging asymmetric total synthesis was achieved by a convergent strategy, in which the tetrahydroindane core of the molecule and an eastern vinyl iodide moiety were combined as the main fragments. The central tetrahydroindane motif was constructed with high stereoselectivity by a bioinspired intramolecular Diels-Alder cycloaddition, generating four stereogenic centers in a single step. The stereocontrol of this key step could be achieved by virtue of a 1,3-allylic strain generated by the temporary introduction of a steric-directing iodine substituent on the substrate. The formation of the macrolactone motif that completes the synthesis was achieved via two different retrosynthetic disconnections, namely, a Suzuki-Miyaura cross-coupling or an alternative Mukaiyama esterification reaction.

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Cite this

Asymmetric Total Synthesis of Antibiotic Elansolid A. / Wang, Liang Liang; Yu, Qi; Zhang, Wenjing et al.
In: Journal of the American Chemical Society, Vol. 144, No. 15, 20.04.2022, p. 6871-6881.

Research output: Contribution to journalArticleResearchpeer review

Wang, LL, Yu, Q, Zhang, W, Yang, S, Peng, L, Zhang, L, Li, XN, Gagosz, F & Kirschning, A 2022, 'Asymmetric Total Synthesis of Antibiotic Elansolid A', Journal of the American Chemical Society, vol. 144, no. 15, pp. 6871-6881. https://doi.org/10.1021/jacs.2c01133
Wang, L. L., Yu, Q., Zhang, W., Yang, S., Peng, L., Zhang, L., Li, X. N., Gagosz, F., & Kirschning, A. (2022). Asymmetric Total Synthesis of Antibiotic Elansolid A. Journal of the American Chemical Society, 144(15), 6871-6881. https://doi.org/10.1021/jacs.2c01133
Wang LL, Yu Q, Zhang W, Yang S, Peng L, Zhang L et al. Asymmetric Total Synthesis of Antibiotic Elansolid A. Journal of the American Chemical Society. 2022 Apr 20;144(15):6871-6881. Epub 2022 Apr 12. doi: 10.1021/jacs.2c01133
Wang, Liang Liang ; Yu, Qi ; Zhang, Wenjing et al. / Asymmetric Total Synthesis of Antibiotic Elansolid A. In: Journal of the American Chemical Society. 2022 ; Vol. 144, No. 15. pp. 6871-6881.
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abstract = "Elansolid A is a structurally complex polyketide macrolactone natural product that exhibits promising antibacterial properties. Its challenging asymmetric total synthesis was achieved by a convergent strategy, in which the tetrahydroindane core of the molecule and an eastern vinyl iodide moiety were combined as the main fragments. The central tetrahydroindane motif was constructed with high stereoselectivity by a bioinspired intramolecular Diels-Alder cycloaddition, generating four stereogenic centers in a single step. The stereocontrol of this key step could be achieved by virtue of a 1,3-allylic strain generated by the temporary introduction of a steric-directing iodine substituent on the substrate. The formation of the macrolactone motif that completes the synthesis was achieved via two different retrosynthetic disconnections, namely, a Suzuki-Miyaura cross-coupling or an alternative Mukaiyama esterification reaction.",
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AU - Yu, Qi

AU - Zhang, Wenjing

AU - Yang, Shuai

AU - Peng, Lin

AU - Zhang, Liang

AU - Li, Xiao Nian

AU - Gagosz, Fabien

AU - Kirschning, Andreas

N1 - Funding Information: Financial support for this work was provided by the Youth Innovation Promotion Association CAS and the High-Level Talent Program of Yunnan Province and in part by the Alexander-von-Humboldt foundation for L.L.W.

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