Total synthesis of Dysidiolide (Danishefsky):
| Reference: | Madnuson, S. R.; Sepp-Lorenzino, L.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 1615. DOI |
| Reactions: | Pd/Sn-Vinyl+Vinyl-X • Carbocupration Alkyne • Cu-Vinyl+Alkyl-X • Singlet oxygen+Diene • Furan+Singlet oxygen • Lactone-5 • CompOx-Furan/Alkene+1ΔO2 • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Wolff-Kishner • Aldehyde → CH3 • Li-Aryl+Aldehyde • Aldehyde+Li-Aryl • Ketone → EnolTriflate • Diels-Alder, Enal • Bicyclo(440) • O-H → O-SiMe2tBu • Alkyl-OH → Aldehyde • Acetal → Aldehyde • |
| Reagents: | Me-Cuprate • HMPA (solvent) • BH(Et)3-Li+ • SiPh2tBu-Cl • Tf2O • EneSulfide • Montmorillonite • Hydrazine • RuO4-Pr4N+, NMO • Furyl-Li • O2 (singlet) • Iodoacetate • Imidazole • SiMe3-OTf • |