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Total synthesis of Pleuromutilin (Part 1):
Reference: Fazakerley, N. J.; Helm, M. D.; Procter, D. J. Chem. Eur. J. 2013, 19, 6718–6723. DOI (Part 2)
Keywords: Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd Cu-R • Seagusa oxidation • Pd-Carboxylation • EnolTriflate → EnoateEster • O-SiMe2tBu → O-H • Radical cyclization(Ketyl) • Cyclopentane • Aldol-Sm • Cyclooctane • O-H → O-SiMe2tBu • Si-Allyl+Aldehyde • Aldehyde+Si-R • Alkyl-OH → Aldehyde • CompRed-CarboxEster/CarboxEster+M-H • Ozonolysis • ConjAdd-Triflation • Cu-Vinyl+Enone • Enone+Cu-Vinyl • ConjAdd-Triflation • ConjAdd Cu-R • Alkyl-OH → Alkyl-OC(O)R • Alkyl-OH → Aldehyde •
Reagents: Allyl-SiR3 • Alkyl-MgX • CuCN • SiMe3-Cl • Pd(OAc)2 • O2 • CuI • Pd(OAc)2 • PPh3 • NEt3 • CO • BF3·OEt2 • TBAT • Piv-Cl • DMAP • HF·Py • Dess-Martin • SmI2 • SiMe2tBu-OTf • NEt3 • AlH4-Li+ • Dess-Martin • O3 • Cu(OAc)2

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