Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation

Kateri A Ahrendt; Robert G Bergman; Jonathan A Ellman

doi:10.1021/ol034228d

Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation

Org Lett. 2003 Apr 17;5(8):1301-3. doi: 10.1021/ol034228d.

Authors

Kateri A Ahrendt¹, Robert G Bergman, Jonathan A Ellman

Affiliation

¹ Center for New Directions in Organic Synthesis, Department of Chemistry and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, University of California, Berkeley, California 94720, USA.

PMID: 12688744
DOI: 10.1021/ol034228d

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Alkenes / chemistry
Catalysis
Cyclization
Gallic Acid / analogs & derivatives*
Gallic Acid / chemistry
Mescaline / analogs & derivatives*
Mescaline / chemical synthesis*
Ruthenium / chemistry

Substances

Alkenes
methyl gallate
Gallic Acid
Ruthenium
Mescaline

Grants and funding

GM50353/GM/NIGMS NIH HHS/United States