Total Synthesis of (±)-Baphicacanthcusine A Enabled by Sequential Ring Contractions
Paul P. Sinclair
Department of Chemistry, University of California, Berkeley, Berkeley, California, 94720 United States
Search for more papers by this authorCorresponding Author
Prof. Dr. Richmond Sarpong
Department of Chemistry, University of California, Berkeley, Berkeley, California, 94720 United States
Search for more papers by this authorPaul P. Sinclair
Department of Chemistry, University of California, Berkeley, Berkeley, California, 94720 United States
Search for more papers by this authorCorresponding Author
Prof. Dr. Richmond Sarpong
Department of Chemistry, University of California, Berkeley, Berkeley, California, 94720 United States
Search for more papers by this authorAbstract
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.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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