4.8 Article

Access to the Pyrroloindoline Core via [3+2] Annulation as well as the Application in the Synthetic Approach to (±)-Minfiensine

Journal

ORGANIC LETTERS
Volume 18, Issue 3, Pages 628-630

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03421

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Funding

  1. Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Tsinghua-Peking Centre for Life Sciences
  2. 1000 Talents Recruitment Program

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A [3 + 2] formal cycloaddition reaction using aza-oxyallyl cation as a synthetic synthon was developed to construct the pyrroloindololine core. With this novel method, a variety of C3-substituted indoles were readily converted into the corresponding pyrroloindoline analogues at room temperature in the mixed solvents. To further demonstrate the utility of this method, a synthetic approach to the total synthesis of (+/-)-minfiensine was developed in quite concise fashion.

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