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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 --- AcOH --- 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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