Total synthesis of (+)-Solamin:
| Reference: | Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 7459-7460. DOI |
| Reactions: | Epoxide+M-SR • Thiolate+Epoxide • Payne rearrangement • O-H → O-SiMe3 • Alkyne Carboruthenation • Lactone-5 • Hydrogenation alkene • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • Alkyl-X+Li-R • Alkyne → Ene-cis (Lindlar) • CompRed-Alkyne/Alkene+M-H • Sharpless epoxidation • Alkyl-OH → Alkyl-I • Ether-5 • Sulfone → α-Halosulfone • Mechanism • O-SiMe3 → O-H • Ramberg-Baecklund • Ether-5 • Hydrogenation alkene • Alkyl-X → Alkyl-SR • Ether-6 • Epoxide+M-OR • Sulfide → Sulfone • |
| Reagents: | Alkynyl-Li • HMPA (solvent) • H2, Pd • Hydroperoxide, tbutyl • Tartrate, diethyl • Thiol, t-butyl • Hg(OAc)2 • Acetic acid, trifluoro • PPh3, I2 • Carbonate, cesium • DMF (solvent) • Perbenzoic acid, 3-chloro • SiMe3-Cl • Ru(cod)Cl • Rh(PPh3)3Cl • H2, Rh • KOtBu • TsOH • H2, Pd • HMPA (solvent) • |