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Total synthesis of Pleuromutilin (Part 1) (Procter):
| Reference: | Fazakerley, N. J.; Helm, M. D.; Procter, D. J. Chem. Eur. J. 2013, 19, 6718–6723. DOI (Part 2) |
| Reactions: | Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd Cu-Alkyl • Mg-R → Cu-R • Saegusa oxidation • Ketone → Enone • Pd-Carboxylation • EnolTriflate → EnoateEster • O-SiMe2tBu → O-H • Radical cyclization(Ketyl) • Cyclopentane • Bicyclo(440) • Aldol-Sm • Cyclooctane • Bicyclo(531) • O-H → O-SiMe2tBu • Si-Allyl+Aldehyde • Aldehyde+Si-R • Alkyl-OH → Ketone • CompRed-CarboxEster/CarboxEster+M-H • Ozonolysis • Cyclohexenone • ConjAdd-Triflation • Cu-Vinyl+Enone • Enone+Cu-Vinyl • ConjAdd Cu-Vinyl • Mg-R → 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 • HOMe (react) • BF3·OEt2 • TBAT • Piv-Cl • DMAP • HF·Py • Dess-Martin • SmI2 • SiMe2tBu-OTf • NEt3 • AlH4-Li+ • Dess-Martin • O3 • Cu(OAc)2 • HOMe (react) • |