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Literature DB >> 12688744

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

Kateri A Ahrendt¹, Robert G Bergman, Jonathan A Ellman.

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.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 12688744 DOI： 10.1021/ol034228d

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. Rhodium catalyzed chelation-assisted C-H bond functionalization reactions.

Authors: Denise A Colby; Andy S Tsai; Robert G Bergman; Jonathan A Ellman
Journal: Acc Chem Res Date: 2011-12-08 Impact factor: 22.384

2. A tethering directing group strategy for ruthenium-catalyzed intramolecular alkene hydroarylation.

Authors: Praveen Kilaru; Sunil P Acharya; Pinjing Zhao
Journal: Chem Commun (Camb) Date: 2018-01-23 Impact factor: 6.222

3. Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates.

Authors: Sze-Sze Ng; Chun-Yu Ho; Timothy F Jamison
Journal: J Am Chem Soc Date: 2006-09-06 Impact factor: 15.419

4. Nonnatural amino acid synthesis by using carbon-hydrogen bond functionalization methodology.

Authors: Ly Dieu Tran; Olafs Daugulis
Journal: Angew Chem Int Ed Engl Date: 2012-04-12 Impact factor: 15.336

5. Rhodium(III)-catalyzed intramolecular hydroarylation, amidoarylation, and Heck-type reaction: three distinct pathways determined by an amide directing group.

Authors: Tyler A Davis; Todd K Hyster; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2013-11-08 Impact factor: 15.336

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

1. Rhodium catalyzed chelation-assisted C-H bond functionalization reactions.

2. A tethering directing group strategy for ruthenium-catalyzed intramolecular alkene hydroarylation.

3. Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates.

4. Nonnatural amino acid synthesis by using carbon-hydrogen bond functionalization methodology.

5. Rhodium(III)-catalyzed intramolecular hydroarylation, amidoarylation, and Heck-type reaction: three distinct pathways determined by an amide directing group.

6. Enantioselective intramolecular hydroarylation of alkenes via directed C-H bond activation.

7. Microbial hydroxylation of o-bromophenylacetic acid: synthesis of 4-substituted-2,3-dihydrobenzofurans.

Review 8. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.