Total synthesis of Sativenediol:
| Reference: | Sigrist, R.; Rey, M.; Dreiding, A. Helv. Chem. Acta 1988, 71, 788. DOI |
| Reactions: | Ketene Cycloaddition • Cyclobutane • Bicyclo(320) • CarboxCl → Ketene • Ketene synthesis • Wolff-Kishner • Ketone → CH2 • Li-Dibromomethyl+Ketone • Allylic oxidation → Allyl-Br • Wohl-Ziegler bromination • Mechanism • Carbene rearrangement • Ti-Allenyl/Propargyl+Ketone • Cyclopentanone • Diels-Alder, Intram, Allene • Diels-Alder, Allene • Bicyclo(221) • Mechanism • Grob fragmentation • Alkene → Diol-1,2 • CompOx-Alkene/Alkene+OsO4 • |
| Reagents: | NEt3 • NBS • CH2Br2 • Me-Li • Hydrazine • OsO4 • LiCHBr2 • Allenyl-Ti • LiTMP • |