Total synthesis of Communesin F:
| Reference: | Yang, J.; Wu, H.; Shen, L.; Qin, Y.. J. Am. Chem. Soc. 2007, 129, 13794. DOI |
| Reactions: | CarboxEster → Alkyl-OH • O-H → O-SiEt3 • O-SiEt3 → O-H • N-Boc → N-H • Friedel-Crafts Acylation • Staudinger • Lactone-6 • Diazoketone • Hydrazone → Diazo • Claisen-Ketene acetal • Oxime → Amine • Lactam-5 • Carboxester → CarboxAmide • Pd-Heck coupling • N-H → N-Allyl • Amine-7 • CarboxAmide → Imidate • CarboxAmide → Amidine • Imidate → Amidine • Amine-6 • Cyclopropane alkylation • Amine-6 • Bicyclo(430)-aza • Cyclopropanation Diazoketone • Lactone-6 • Bicyclo(310)-aza • CarboxEster epimerization • Lactone → Ketene acetal • Lemieux-Johnson oxidation • Alkene cleavage • Ketone → CH2 • CarboxEster → Alkyl-OH • CarboxCl → CarboxEster • O-H → O-C(O)R • Alkyl-OH → Aldehyde • Aldehyde → Oxime • Oxime → Amine • N-H → N-Boc • N-H → N-Me • Aldehyde → Oxime • N-H → N-C(O)OR • N-C(O)R → N-H • Imine → Amine • N-H → N-C(O)R • Ketone → Hydrazone • |
| Reagents: | Oxalyl chloride • HOMe (react) • AlH4-Li+ • SiEt3-Cl • MeI • Fluoride, R4N+ • Bisulfate, R4N+ • Hydrazine, tosyl • TsOH • DBU • CuOTf • PBu3 • O=C(OMe)Cl • DMAP • NaH • Allyl-Br • OsO4, NaIO4 • NH2OH • H2, RaNi • Dess-Martin • NH2OH • H2, RaNi • Boc2O • Pd(OAc)2 • P(Tol)3 • NEt3 • TsOH·Py • Et3O+ X- • NEtiPr2 • SiO2 • Acetic acid, trifluoro • Hydroxide, potassium • BH4-Na+ • Carbonate, sodium • NaOMe • DMAP • |