Total Synthesis of (±)-Baphicacanthcusine A Enabled by Sequential Ring Contractions.
Angew Chem Int Ed Engl
; : e202409139, 2024 Jul 12.
Article
em En
| MEDLINE
| ID: mdl-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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MEDLINE
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En
Ano de publicação:
2024
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Article