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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: Ketone → EnolSilane • Alkyl-OH → Aldehyde • Krapcho Decarboxylation • Decarboxylation • Saegusa oxidation • Ketone → Enone • Ketone → Ketal(thio) • Ketal(thio) → CH2 • Ketone → CH2 • Lactone → Alkyl-OH • O-H → O-SiMe2tBu • Alkyl-OH → Ketone • Ketone+Li-Alkyl • Li-Me+Ketone • O-SiMe2tBu → O-H • Mitsunobu → Ether • Alkyl-OH → Alkyl-OR • Ether-5 • Aldol-enamine → Enone • ConjAdd Cu-R • Enone+Cu-Me • Saegusa oxidation • Ketone → Enone • Wittig-carboxymethyl → EnoateEster • Diazoester ring expansion • ConjAdd M-OR • Ketone enolate+EnoateEster • Diels-Alder, Intram •
Reagents: LiCuMe2 • LiNiPr2 • SiMe3-Cl • O2 • Acetic acid • Cr2O7·2PyH (PDC) • PPh3=C(Me)-CO2R • Diazoacetate • BF3·OEt2 • MgCl2 • DMSO (solvent) • SiMe2tBu-OTf • Pd(OAc)2 • Hydroxide, sodium • HCl • Thiol, (CH2)2-SH • BF3·OEt2 • RaNi • AlHiBu2 • SiMe2tBu-OTf • RuO4-Pr4N+, NMO • MeLi • Fluoride, R4N+ • PPh3, DEAD • SiMe3-Cl • ZnCl2

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