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Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone

Author

Listed:
  • Zhezhe Xu

    (Lanzhou University)

  • Weibo Peng

    (Lanzhou University)

  • Jiarui Huang

    (Lanzhou University)

  • Jinhui Shen

    (Lanzhou University)

  • Jing-Jing Guo

    (Lanzhou University)

  • Anhua Hu

    (Lanzhou University)

Abstract

Electronically mismatched Diels−Alder reaction between two electron-deficient components is synthetically useful and yet underdeveloped under thermal conditions. Herein, a photoinduced formal [4 + 2] cycloaddition of enone with a variety of electron-deficient dienes is described. Key to the success of this stepwise methodology relies on a C − C bond cleavage/rearrangement of the cyclobutane based overbred intermediate via diversified mechanistic pathways. Based on this annulation method, total synthesis of lucidumone is achieved in nine steps.

Suggested Citation

  • Zhezhe Xu & Weibo Peng & Jiarui Huang & Jinhui Shen & Jing-Jing Guo & Anhua Hu, 2024. "Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-54117-0
    DOI: 10.1038/s41467-024-54117-0
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    1. Stone Woo & Ryan A. Shenvi, 2022. "Synthesis and target annotation of the alkaloid GB18," Nature, Nature, vol. 606(7916), pages 917-921, June.
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