Total synthesis of Urechitol A New:
| Reference: | Sumiya, T.; Ishigami, K.; Watanabe, H. J. Am. Chem. Soc. 2010, 49, 5527-5528. DOI |
| Reactions: | Oxyallyl Cycloaddition • Ether-5 • Cycloheptane • Bicyclo(321)-oxa • Epoxidation, V • Epoxide → Diol • Ketone → Ketal(Me) • O-H → O-SiMe2tBu • Alkyl-OH → Aldehyde • Mg-Allyl+Aldehyde • Aldehyde+Mg-R • Williamson etherification • O-H → O-Me • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • Mg-Alkyl+Aldehyde • Aldehyde+Mg-R • Alkene cleavage • Lemieux-Johnson oxidation • O-Bn → O-H • |
| Reagents: | TiCl4 • Hydroperoxide, tbutyl • VO(acac)2 • Bicarbonate, sodium • Bicarbonate, sodium • TsOH • HOMe (react) • SiMe2tBu-Cl • Imidazole • RuO4-Pr4N+, NMO • Allyl-MgX • NaH • MeI • Fluoride, R4N+ • RuO4-Pr4N+, NMO • Me-MgCl • OsO4, NaIO4 • Lutidine • H2, Pd • |