Water overcomes methyl group directing effects in epoxide-opening cascades.
Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect of a methyl substituent at either site of the epoxide, making water a uniquely versatile medium and promoter of epoxide opening.
Morten
Christopher J
CJ
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Jamison
Timothy F
TF
D001688:Biological Products / Q000138:chemical synthesis*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D008387:Marine Toxins / Q000096:biosynthesis / Q000138:chemical synthesis / Q000737:chemistry; D008697:Methane / Q000737:chemistry*; D035964:Oxocins / Q000138:chemical synthesis / Q000737:chemistry; D014867:Water / Q000737:chemistry*; D000095702:Polyether Toxins
D001688:Biological Products; D004852:Epoxy Compounds; D008387:Marine Toxins; D008697:Methane; D035964:Oxocins; D014867:Water; C043466:brevetoxin B; D000095702:Polyether Toxins