Total synthesis of Phomactin R New:
| Reference: | Kuroda, Y.; Nicacio, K. J.; da Silva, I. A.; Leger, P. R.; Chang, S.; Gubiani, J. R.; Deflon, V. M.; Nagashima, N.; Rode, A.;Blackford, K.; Ferreira, A. G.; Sette, L. D.; Williams, D. E.; Andersen, R. J.; Jancar, S.; Berlinck, R. G. S.; Sarpong, R. Nature Chemistry 2018, 10, 938-945. DOI |
| Reactions: | Carboalumination Alkyne • Al-Vinyl → I-Vinyl • O-H → O-SiMe2tBu • Li/I → Li-Vinyl • Epoxidation, peracid • Epoxide+Ketyl • Cyclobutane • Bicyclo(311) • Alkyl-OH → Alkyl-SR • Cyclobutane opening • Cyclohexenone • Sulfide → Sulfone • Li-Me+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Ketone → CH2 • Allylic oxidation → Enal • Li-Vinyl+Aldehyde • O-H → O-SEM • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Li-Sulfone+Aldehyde • Bicyclo(931) • Cyclododecane • Alkyl-SO2R → Alkyl-H • O-SEM → O-H • Allyl-OH → Enal • Luche reduction • Enone → Allyl-OH • Epoxidation, V • CompOx-Alkene/Alkene+M-OOR • Allyl-OH → Enone • Allyl-OH → Allyl-Br • |
| Reagents: | AlMe3 • ZrCp2Cl2 • I2 • SiMe2tBu-Cl • Perbenzoic acid, 3-chloro • TiCp2Cl2 • Disulfide, phenyl • PBu3 • Rh(cod)OH)2 • Mo7O24(NH4)6 • BuLi(tert) • Me-Li • Burgess reagent • SEM-Cl • Fluoride, R4N+ • Sulfonyl chloride, methane • Bromide, lithium • NaN(SiMe3)2 • Fluoride, R4N+ • DMPU (solvent) • Na(Hg) • MnO2 • BH4-Na+, CeCl3 • Dess-Martin • Vinyl-I • Vinyl-Li • |