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Total synthesis of (+)-Solamin:
Reference: Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 7459-7460. DOI
Keywords: Payne rearrangement • O-H → O-SiMe3 • Alkyne Carboruthenation • Lactone-5 • Hydrogenation alkene • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • Alkyl-X+Li-R • Hydrogenation Lindlar • Sharpless epoxidation • Alkyl-OH → Alkyl-I • Ether-5 • O-SiMe3 → O-H • Ramberg-Baecklund • Hydrogenation alkene •
Reagents: Alkynyl-Li • HMPA (solvent) • H2, Pd • Hydroperoxide, tbutyl • DEET • Ti(OiPr)4 • 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 •

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