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Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C–H/C–H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F
- Source :
- J Am Chem Soc
- Publication Year :
- 2021
- Publisher :
- American Chemical Society (ACS), 2021.
-
Abstract
- The development of practical C−H/C−H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C−C bonds. Herein, we report a cyclative C(sp3)−H/C(sp2)−H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-N-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na2CO3·1.5H2O2) as the sole oxidant, generating water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, could be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through the sequential functionalizations of four C−H bonds.
- Subjects :
- Pivalic acid
Molecular Structure
Tetrahydronaphthalenes
Indane
Total synthesis
Stereoisomerism
General Chemistry
Sodium percarbonate
Phenylacetic acid
Biochemistry
Combinatorial chemistry
Article
Catalysis
Coupling reaction
chemistry.chemical_compound
Colloid and Surface Chemistry
chemistry
Cyclization
Indans
Organometallic Compounds
Chromane
Chromans
Cyclopentane
Subjects
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 143
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....0718eac535fb5df4935553bb3a5482d4