Total synthesis of Brasilicardin C (Part 1) New:
| Reference: | Yoshimura, F.; Itoh, R.; Torizuka, M.; Mori, G.; Tanino, K. Angew. Chem. Int. Ed. 2018, 57, 17161-17167. DOI (Part 2) |
| Reactions: | Corey-Fuchs • Alkyl-OH → Aldehyde • HWE → EnoateEster • Sharpless dihydroxylation • Alkene → Diol-1,2 (asym) • O-H → O-MOM • CarboxEster → Alkyl-OH • Alkyl-OH → Alkyl-I • Nitrile anion+Alkyl-X • O-H → O-SiMe2tBu • Alkyl-OH → Aldehyde • HWE → EnoateAmide • Nirile anion+EnoateAmide • ConjAdd Nirile anion • Cyclohexane • CarboxAmide(Weinreb) → Aldehyde • Wittig-methoxymethyl • EnolEther → Aldehyde • Wittig-methyl • Nitrile → Aldehyde • Aldehyde → Alkyl-OH • Hydrocycanation Alkene • Alkyl-OH → Aldehyde • HWE → EnoateEster-cis • CarboxEster → CarboxAcid • CarboxAcid → CarboxAmide (Weinreb) • Nirile anion+EnoateAmide • ConjAdd Nirile anion • Cyclohexane • Bicyclo(440) • O-H → O-SiiPr3 • CarboxAmide(Weinreb) → Aldehyde • CompRed-Carboxamide/Nitrile+M-H • Nitrile → Aldehyde • HWE → EnoateEster • Cu-Me+Vinyl-X • Cu-Vinyl+EnoateEster • Cyclohexene • |
| Reagents: | DMSO, (COCl)2 (Swern) • NEt3 • P(O)(OR)2CH2-C(O)OR' • Fe(CN)6K3 • Chloromethyl ether • NEtiPr2 • AlH4-Li+ • DBU • I2 • Imidazole • HMPA (solvent) • RuO4-Pr4N+ • NMO • Fluoride, R4N+ • NaN(SiMe3)2 • AlHiBu2 • PPh3=CH-OR • KOtBu • TsOH • PPh3=CH2 • KOtBu • AlHiBu2 • AlHiBu2 • RuO4-Pr4N+ • NMO • NaN(SiMe3)2 • Hydroxide, lithium • Carbodiimide • HOAT • NaN(SiMe3)2 • SiiPr3-Cl • HSiPhH2 • Pyridine, 2,6-di-tBu • Fluoride, R4N+ • AlHiBu2 • P(O)(OR)2CH2-C(O)OR' • NaN(SiMe3)2 • PPh3, CBr4 • PPh3=CBr2 • Me-Cuprate • AlHiBu2 • Sulfonamide, methane • NaN(SiMe3)2 • |