Total synthesis of Gracilioether F New:
| Reference: | Shen, X.-Y.; Peng, X.-S.;Wong*, H. N. C.; Org. Lett. 2016, 18, 1032-1035. DOI |
| Reactions: | Iodolactonization • Lactone-5 • Lactone → Ketene acetal • Furan synthesis • Ketene acetal+Alkyl-X • Friedel-Crafts Alkylation • Hydroboration → Alkyl-OH • Alkyl-OH → Aldehyde • Wittig-methyl • Lactone → Lactol • Lactol → Ether • Ether-5 • Pd-Heck coupling • Cyclopentane • Bicyclo(330)-oxa • Singlet oxygen+Diene • Diimide+Alkene • Peroxide reduction • Alkyl-OH → CarboxAcid • Lactone-5 • |
| Reagents: | Acetonitrile (solvent) • LiN(SiMe3)2 • SiiPr3-Cl • Allyl-Br • AgOC(O)CF3 • BH-BBN • H2O2, NaOH • Dess-Martin • Bicarbonate, sodium • DBU • PPh3=CH2 • LiN(SiMe3)2 • AlHiBu2 • HSiEt3 • BF3·OEt2 • Pd(OAc)2 • PPh3 • Carbonate, potassium • O2 (singlet) • Photochemistry • Diimide • Acetic acid • Zn° • Acetic acid • CrO3 • Acetic anhydride • Acetic acid • |