Total synthesis of Hypnophilin New:
| Reference: | Geng, F.; Liu, J.; Paquette, L. A. Org. Lett. 2002, 4, 71-73. DOI |
| Reactions: | Mechanism • Li-Vinyl+Ketone • Enone+Li-R • Li-Vinyl+Ketone • Enone+Li-R • EnolEther → Ketone • CompNu-EnolEther/EnolEther+H+ • Allyl-OH → Allyl-Cl • Allyl-X → Allyl-H • Enone-β-OR+Al-H • Enone-β-OR → Enone • Stork-Danheiser • O-H → O-MOM • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Li-Me+Ketone • Enone+Li-R • Dehydration → Enone • Enone → EnolSilane • Saegusa oxidation • Ketone → Enone • Enone epoxidation, nucleophilic • Aldol-Acid → Aldol • Cyclopentenone • Cyclopentane • Electrocyclic-4π • Electrocyclic-8π • Cyclooctane • Retro-Michael • |
| Reagents: | Vinyl-Li • Chloride, ammonium • H2SO4 • Sulfonyl chloride, methane, NEt3 • DMAP • Li°/NH3 • AlH4-Li+ • HCl, H2O • Chloromethyl ether • NEtiPr2 • LiNiPr2 • MeI • HMPA (solvent) • Me-Li • H2SO4 • LiNiPr2 • DMPU (solvent) • SiMe3-Cl • Pd(OAc)2 • H2O2, K2CO3 • |