Synthesis of aza-, oxa-, and thiabicyclo[3.1.0]hexane heterocycles from a common synthetic intermediate.
[reaction: see text] An efficient and stereospecific approach to the synthesis of structurally constrained aza-, oxa-, and thiabicyclo[3.1.0]hexane heterocycles has been achieved through application of the intramolecular cyclopropanation reaction of diazoacetates. The various constrained heterocycles (X = N, O, or S) are conveniently prepared from a common diol intermediate accessible from readily available cinnamyl alcohols. Application of the methodology to the synthesis of conformationally constrained oxazolidinone antibacterials is also discussed.
Renslo
Adam R
AR
Department of Medicinal Chemistry, Vicuron Pharmaceuticals, Fremont, California 94555, USA. arenslo@vicuron.com
Gao
Hongwu
H
Jaishankar
Priyadarshini
P
Venkatachalam
Revathy
R
Gordeev
Mikhail F
MF
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D001372:Aza Compounds / Q000138:chemical synthesis; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000494:pharmacology; D010100:Oxygen / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013457:Sulfur Compounds / Q000138:chemical synthesis
D000900:Anti-Bacterial Agents; D001372:Aza Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D023303:Oxazolidinones; D020005:Propanols; D013457:Sulfur Compounds; D010100:Oxygen; C020722:cinnamyl alcohol