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Total synthesis of Sativenediol:
Reference: Sigrist, R.; Rey, M.; Dreiding, A. Helv. Chem. Acta 1988, 71, 788. DOI
Keywords: Ketene Cycloaddition • Cyclobutane • 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 • Diels-Alder, Allene • Bicyclo(221) • Mechanism • Grob fragmentation • Alkene → Diol-1,2 • CompOx-Alkene/Alkene+OsO4
Reagents: NEt3 • NBS • CH2Br2 • MeLi • Hydrazine • OsO4 • LiCHBr2 • Allenyl-Ti • LiTMP •

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