Synthesis of a Tricyclic Mescaline Analogue by Catalytic C−H Bond Activation
Organic Letters – March 22, 2003
Source: OpenAlex
Summary
A tetrahydrobis(benzofuran) mescaline analogue was synthesized in six steps with a notable 38% overall yield from (4'-O-methyl)methyl gallate. The pivotal step involved a tandem cyclization reaction utilizing directed C–H activation, followed by olefin insertion. This innovative approach enhances the efficiency of combinatorial chemistry and catalysis, potentially aiding in medicinal chemistry applications, including HIV/AIDS drug development and treatment. The study showcases advancements in stereochemistry and catalytic methods critical for the synthesis and biological evaluation of therapeutic compounds.
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.