Total synthesis of 8,14-Cedranoxide:
| Reference: | Ihara, M.; Makita, K.; Takasu, K. J. Org. Chem. 1999, 64, 1259 DOI |
| Reactions: | O-SiMe2tBu → O-H • Decarboxylation Krapcho • Ketone → Ketal(thio) • O-SiMe2tBu → O-H • Mitsunobu → OR • Alkyl-OH → Alkyl-OR • Aldol-enamine → Enone • ConjAdd Cu-Me • Enone+Cu-Me • Saegusa oxidation • Ketone → Enone • Wittig-carboxymethyl → EnoateEster • CompE+-Aldehyde/Ketone+Wittig • Diazoester ring expansion • Bicyclo(321) • ConjAdd M-OR • Lactone-5 • Ketone enolate+EnoateEster • Diels-Alder, Intram, Ene • Bicyclo(221) • Bicyclo(330) • Cyclopentane • Ketal(thio) → CH2 • Ketone → CH2 • Saegusa oxidation • Ketone → Enone • Ketone → EnolSilane • Lactone → Alkyl-OH • Ketone+Li-Alkyl • Li-Me+Ketone • Ether-5 • Ketone → Ketal(thio) • CompE+-Ketone/Lactone+glycol • Alkyl-OH → Aldehyde • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • Alkyl-OH → Ketone • CarboxEster → CarboxAcid • Ketone → EnolSilane • |
| Reagents: | Me-Cuprate • LiNiPr2 • SiMe3-Cl • O2 • Acetic acid • Cr2O7·2PyH (PDC) • PPh3=C(Me)-CO2R • Diazoacetate • BF3·OEt2 • MgCl2 • DMSO (solvent) • SiMe2tBu-OTf • O2 • Hydroxide, sodium • HCl, H2O • Thiol, (CH2)2-SH • BF3·OEt2 • RaNi • AlHiBu2 • SiMe2tBu-OTf • RuO4-Pr4N+, NMO • Me-Li • Fluoride, R4N+ • PPh3, DEAD • SiMe3-Cl • ZnCl2 • |