Total synthesis of Aplykurodinone-1:
| Reference: | Xu, B.; Xun, W.; Wang, T.; Qiu, F. G. Org. Lett. 2017, 19, 4861-4863. DOI |
| Reactions: | CarboxEster → Ketene acetal • Claisen-Ireland • Alkyl-OH → Aldehyde • O-H → O-C(O)R • CarboxEster → Alkyl-OH • Wittig-methoxymethyl • EnolEther → Aldehyde • Prins • Cyclopentane • Bicyclo(430) • Epoxidation, V • Alkyl-OH → Ketone • Epoxide → Allyl-OH • Dehydroalkoxylation → Enone • O-H → O-C(O)R • Michael Enone • ConjAdd Enolate • Lactone-5 • Decarboxylation Krapcho • |
| Reagents: | Carbodiimide • DMAP • LiNiPr2, HMPA • SiMe2tBu-Cl • Dess-Martin • PPh3=CH-OR • TsOH • NaN(SiMe3)2 • Hydroperoxide, tbutyl - V • Dess-Martin • DBU • Malonate • PPh3, DIAD • Chloride, sodium • DMSO (solvent) • Acetonitrile (solvent) • |