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  • Title: Total Synthesis of (±)-Baphicacanthcusine A Enabled by Sequential Ring Contractions.
    Author: Sinclair PP, Sarpong R.
    Journal: Angew Chem Int Ed Engl; 2024 Oct 07; 63(41):e202409139. PubMed ID: 38994548.
    Abstract:
    Reported herein is the first total synthesis of the poly-pseudoindoxyl natural product baphicacanthcusine A. The synthesis leverages the oxidative rearrangement of indoles to pseudoindoxyls to install vicinal pseudoindoxyl heterocycles in a diastereoselective manner. Key steps include an acid-mediated cyclization/indole transposition, two diastereoselective oxidative ring contractions, and a site-selective C-H oxygenation. The synthesis of the oxidation precursors was guided by recognition of an element of hidden symmetry. This work provides a foundation for the chemical synthesis of other poly-pseudoindoxyl alkaloids.
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