Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation.
[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.
Ahrendt
Kateri A
KA
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.
Bergman
Robert G
RG
Ellman
Jonathan A
JA
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005707:Gallic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D008635:Mescaline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry
D000475:Alkenes; C052082:methyl gallate; D005707:Gallic Acid; D012428:Ruthenium; D008635:Mescaline