Total synthesis of Mycotrienol (Part 1) New:
| Reference: | Masse, C. E.; Yang, M.; Solomon, J.; Panek, J. S. J. Am. Chem. Soc. 1998, 120, 4123-4134. DOI (Part 2) |
| Reactions: | Acetal → Acetal • Si-Allyl+Oxonium • CarboxEster enolate+Ketone • O-H → O-C(O)R • Ozonolysis • Si-Allyl+Aldehyde • Aldehyde+Si-R • O-H → O-SiiPr3 • Ozonolysis • Aldehyde → Acetal(Me) • O-Bn → O-H • Lactone-5 • Lactone → Alkyl-OH • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Alkyl-OH → Alkyl-I • Dehydroacetoxylation → EnoateEster • Aldehyde → Alkyl-OH • CompRed-Aldehyde/Nitro+M-H • Benzyl-OH → Benzyl-Br • Alkyl-X → Alkyl-SO2R • Nitro → Amine • N-H → N-C(O)R • Lactone → CarboxAmide • O-H → O-SiMe2tBu • |
| Reagents: | TsOH • SiMe3-OTf • CH2=C(OLi)(OR) • LiN(SiMe3)2 • Acetic anhydride, NEt3 • DMAP • O3; Me2S • Allyl-SiR3 • TiCl4 • SiiPr3-OTf • O3 • HOMe (react) • TsOH • H2, Pd • AlH4-Li+ • TMEDA • SiMe2tBu-OTf • HF·Py • MeI • DBU • BH3·THF • PPh3, CBr4 • Sulfinate, benzene • H2, Pd • AlMe3 • SiMe2tBu-Cl • Imidazole • |