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Synthesis of a Tricyclic Mescaline Analogue by Catalytic C−H Bond Activation

Kateri A. Ahrendt, Robert G. Bergman, Jonathan A. Ellman

Organic Letters March 22, 2003 DOI: 10.1021/ol034228d (opens in new tab)

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AI-extracted from the abstract
Characteristics Synthesis and biological evaluation Peer reviewed
Topics Mescaline
Keywords Yield engineering Tricyclic Olefin fiber Tandem Benzofuran Catalysis Stereochemistry Medicinal chemistry Combinatorial chemistry Organic chemistry
Citations 99
Key points A tetrahydrobis(benzofuran) mescaline analogue was prepared in six steps and 38% overall yield via a tandem cyclization using directed C–H activation and olefin insertion.

Abstract

[reaction: see text] A tetrahydrobis(benzofuran) mescaline analogue has been prepared in six steps and 38% overall yield from (4'-O-methyl)methyl gallate. The key step in this synthesis is a tandem cyclization reaction via directed C[bond]H activation followed by olefin insertion.

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