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 via OpenAlex
Summary
AI-generated from the abstractA tetrahydrobis(benzofuran) mescaline analogue was synthesized in six steps with a 38% overall yield starting from (4'-O-methyl)methyl gallate. The key step involved a tandem cyclization reaction using directed C–H activation followed by olefin insertion. This approach demonstrates an efficient route to a tricyclic compound related to mescaline.
Study at a glance
| Characteristics | Synthesis and biological evaluation Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Yield engineering Tricyclic Olefin fiber Tandem |
| Citations | 99 |
| Key finding | 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.