Total synthesis of Dendrowardol C:
| Reference: | Wolleb, H.; Carreira, E. M. Angew. Chem. Int. Ed. 2017, 56, 10890 -10893. DOI |
| Reactions: | O-H → O-SiMe3 • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Aldol-Na → Aldol • Cyclopentanone • Bicyclo(321) • Alkyl-OH → Ketone-1,3-di • Wittig-methoxymethyl • CompE+-Ketone/Ketone+Wittig • EnolEther → Aldehyde • Aldehyde+Li-Vinyl • Felkin-Anh • CompE+-Aldehyde/Ketone+M-R • Epoxidation, V • CompOx-Alkene/Alkene+M-OOR • Epoxide+Enolate • Ketone enolate+Epoxide • Cyclopentane • Bicyclo(221) • O-H → O-Tf • Ketyl+Alkyl-X • Cyclobutane • Bicyclo(320) • O-H → O-SiMe3 • Hydroboration → Alkyl-OH • O-SiMe3 → O-H • |
| Reagents: | AlH4-Li+ • DMSO, (COCl)2 (Swern) • NEt3 • NaOMe • Dess-Martin • PPh3=CH-OR • BuLi(n) • HCl, H2O • Vinyl-Li • Hydroperoxide, tbutyl - V • LiNiPr2, HMPA • Tf2O • SiMe3-Cl • Li°/Naphth • SiMe3-Cl • DMAP • BH(Pinacol) • NaBO3 • HCl, H2O • |