Total synthesis of Aspicillin:
| Reference: | Oppolzer, W.; Radinov, R. N.; DeBrabander, J. Tetrahedron Lett. 1995, 36, 2607. DOI |
| Reactions: | O-THP → O-H • Selenide → Selenoxide • O-SiMe2tBu → O-H • Acetoxonium • Mg-Alkyl+Epoxide • Epoxide+Mg-R • Mg-R → Cu-R • CarboxEster → Ketene acetal • Selenoxide-Ei → EnoateEster • CarboxEster → EnoateEster • Epoxidation, V • Epoxide → Diol • Hydroboration Alkyne • CompRed-Alkene/Aldehyde+M-H • B-R → Zn-R • Zn-Vinyl+Aldehyde • Aldehyde+Zn-R • Lactone-9+ • CompE+-Aldehyde/CarboxEster+M-R • CarboxAcid → CarboxEster • Alkyl-OH → Aldehyde • O-H → O-C(O)R • O-H → O-SiMe2tBu • O-C(O)R → O-H • |
| Reagents: | Epoxide • Alkyl-MgX • CuCl(cod) • Carbodiimide • TsOH • DMSO, (COCl)2 (Swern) • Chiral catalyst (amino-alcohol) • DBU • LiNiPrCy • SiMe2tBu-Cl • SePh-Br • Perphthalic acid • HF • Hydroperoxide, tbutyl - V • Acetic anhydride • BF3·OEt2 • Bicarbonate, sodium • HCl, MeOH • Vinyl-ZnX • |