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Synapse
May 3, 20267 citations

Precision indole skeletal editing for single-carbon replacement.

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LZLing ZhangYLYatao LangZLZhen Luo

Key Points

  • To explore precision indole skeletal editing for effective carbon replacement.
  • Four-step total synthesis of quebrachamine performed.
  • Experimental studies conducted alongside density functional theory (DFT) calculations.
  • Reaction pathways studied included cascade [2+2] cycloaddition and retro-[2+2] ring opening.
  • Elucidation of an atomic-level reaction pathway for synthesis.
  • Successful application in the synthesis of quebrachamine reported.

Abstract

C-labeled carbon into the scaffold. We highlighted the practical applicability of this method through a concise four-step total synthesis of quebrachamine, a complex monoterpene indole alkaloid. Experimental studies and density functional theory (DFT) calculations revealed a reaction pathway involving cascade 2+2 cycloaddition, retro-2+2 ring opening, decarbonylation, and cyclization, elucidating the sequence at an atomic level.

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Cite This Study

Zhang et al. (2026) studied this question.

synapsesocial.com/papers/69f6e60f8071d4f1bdfc6b41https://doi.org/10.1126/science.aec3587
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