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Total synthesis of 8,14-Cedranoxide:
Reference: Ihara, M.; Makita, K.; Takasu, K. J. Org. Chem. 1999, 64, 1259 DOI
Keywords: Alkyl-OH -> Aldehyde • Krapcho Decarboxylation • Decarboxylation • Saegusa oxidation • Ketone -> Ketal(thio) • Ketal(thio) -> CH2 • Lactone -> Alkyl-OH • O-H -> O-SiMe2tBu • Alkyl-OH -> Ketone • Ketone+Li-Me • O-SiMe2tBu -> O-H • Mitsunobu -> Ether • Alkyl-OH -> Alkyl-OR • Ether-5 • Aldol-enamine • ConjAdd Cu-R • Enone+Cu-Me • Saegusa oxidation • Wittig-carboxymethyl -> EnoateEster • Ketone enolate+EnoateEster • Diazoester ring expansion • ConjAdd M-OR •
Reagents: LiCuMe2 • LiNiPr2 • SiMe3-Cl • O2 • Acetic acid • Cr2O7·2PyH (PDC) • Ph3P=C(Me)-CO2R • SiMe3-Cl • ZnCl2 • Diazoacetate • BF3·OEt2 • MgCl2 • DMSO (solvent) • SiMe2tBu-OTf • Pd(OAc)2 • Hydroxide, sodium • HCl • HS-(CH2)2-SH • BF3·OEt2 • RaNi • AlHiBu2 • SiMe2tBu-OTf • RuO4-Pr4N+, NMO • MeLi • Fluoride, Bu4N+ • PPh3, DEAD •

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