Microwave-assisted synthesis of substituted tetrahydropyrans catalyzed by ZrCl4 and its application in the asymmetric synthesis of exo- and endo-brevicomin.
The ZrCl4-catalyzed deprotection of 1,3-dioxane/dioxalane and the simultaneous formation of 6-methoxy-substituted tetrahydropyrans proceeded under microwave irradiation in good yield. This synthetic methodology was used for the asymmetric synthesis of (+)-exo- and (+)-endo-brevicomin in 55% overall yield over 4 steps.
Singh
Surendra
S
Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland.
Guiry
Patrick J
PJ
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D008872:Microwaves; D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D002712:Chlorides; D011714:Pyrans; D015040:Zirconium; C012219:brevicomin; C429984:zirconium chloride