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Total synthesis of Pleuromutilin (Part 2):
Reference: Fazakerley, N. J.; Helm, M. D.; Procter, D. J. Chem. Eur. J. 2013, 19, 6718–6723. DOI (Part 1)
Keywords: Hydrogenation Alkene • O-H → O-SiPh2tBu • O-H → O-C(O)R • CompNu-Alcohol/Alcohol+RC(O)X • Alkyl-OH → Alkyl-H • Ketone → EnolSilane • Ketone → EnolSilane • Rubottom oxidation • Ketone → Ketone-α-OR • O-SiMe2tBu → O-H • O-H → O-MOM • Li/Sn → Li-Vinyl • Li-Vinyl+Ketone • Ketone+Li-Vinyl • O-MOM → O-H • Allyl-OH → Allyl-Cl • Corey-Kim • Cu-Me+Allyl-X • Alkyl-OH → Alkyl-OC(O)R • EnolEther → Enal • CarboxEster → Alkyl-OH • Ketone → Ketal • O-H → O-C(S)NR2 • Enal → Allyl-OH • O-C(O)R → O-H • Alkyl-OH → Ketone • O-H → O-C(O)R •
Reagents: Glycol • Vinyl-SnR3 • Acetic acid • Acyl imidazole • H2, Pd • SmI2 • Pyrrolidine • LiNiPr2 • Benzoyl chloride • HSnBu3 • AIBN • FeCl3 • NH(SiMe3)2 (HMDS) • SiMe3-I • Bicarbonate, sodium • Perbenzoic acid, 3-chloro • HF • Chloromethyl ether • NEtiPr2 • BuLi(n) • FeCl3 • BH4-Na+ • NCS • CuCN • AlH4-Li+ • Dess-Martin • Acetyl chloride • DMAP • S=C(Imid)2

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