Total synthesis of Cephanolide C:
| Reference: | Xu, L.; Wang, C.; Gao, Z.; Zhao, Y.-M. J. Am. Chem. Soc. 2018, 140, 5653-5658. DOI |
| Reactions: | Pd/Zn-Alkyl+Aryl-X • Aryl-H → Aryl-I • Claisen acylation, formate • CarboxEster enolate+Formate • Robinson annulation, ketoester • KetoEster enolate+Enone • Enone → Allyl-OH • CarboxEster → CarboxAcid • Lactone-6 • Bicyclo(222)-oxa • Lactone → Lactol • Lactol → Acetal • Pd-Carbonylative annulation • Cyclopentanone • Cyclohexane • Bicyclo(430) • Lactol → Lactone • Lactone-6 • Ketone → CH2 • CompRed-Ketone/Lactone+M-H • Benzylic oxidation → Benzyl-OR • Benzylic oxidation → Ketone • O-Me → O-H (phenol) • O-H → O-Tf (phenol) • Aryl-OTf → Aryl-H • |
| Reagents: | Alkyl-ZnX • Pd(OAc)2 • I2 • AgOAc • Formate, methyl • LiNiPr2 • Methyl vinyl ketone • Cu(OTf)2 • BH4-Na+, CeCl3 • Hydroxide, sodium • Carbodiimide • AlHiBu2 • TsOH·Py • HOMe (react) • Pd(OAc)2 • CO • BF3·OEt2 • TfOH • HSiEt3 • DDQ • CrO3Cl·PyH (PCC) • B(Cl)3 • Tf2O • Pd(OAc)2 • HSiEt3 • Perbenzoic acid, 3-chloro • |