Indium tribromide-promoted arene-terminated epoxy olefin cyclization.
An arene-terminated epoxy olefin cyclization was promoted by a water-tolerant Lewis acid to give tri- and tetracyclic 3beta-hydroxy terpenoids and steroid derivatives in 57 and 37% yields, respectively, per new formed ring up to 75%.
Zhao
Jun-Feng
JF
Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore.
Zhao
Yu-Jun
YJ
Loh
Teck-Peng
TP
D000475:Alkenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007204:Indium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D012997:Solvents; D013256:Steroids / Q000138:chemical synthesis; D013729:Terpenes / Q000138:chemical synthesis
D000475:Alkenes; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D012997:Solvents; D013256:Steroids; D013729:Terpenes; D007204:Indium