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Total synthesis of Communesin F:
Reference: Yang, J.; Wu, H.; Shen, L.; Qin, Y.. J. Am. Chem. Soc. 2007, 129, 13794. DOI
Keywords: CarboxEster → Alkyl-OH • O-H → O-SiEt3 • N-H → N-Me • O-SiEt3 → O-H • N-H → N-C(O)OR • Alkene cleavage • Aldehyde → Oxime • Alkyl-OH → Aldehyde • Aldehyde → Oxime • N-H → N-Boc • N-Boc → N-H • N-H → N-C(O)R • Imine → Amine • Friedel-Crafts Acylation • Staudinger • Diazoketone • Claisen-Ketene acetal • Reductive amination, H2 • N-H → N-Alkyl • Lactam-5 • Reductive amination, H2 • Pd-Heck coupling • N-H → N-Alkyl • Amine-7 • CarboxAmide → Imidate • CarboxAmide → Amidine • Imidate → Amidine • Cyclopropane alkylation • Amine-6 • Cyclopropanation Diazoketone • Lactone-6 • CarboxEster epimerization • CarboxEster → Ketene acetal • Lemieux-Johnson oxidation • Ketone → CH2
Reagents: Oxalyl chloride • AlH4-Li+ • SiEt3-Cl • MeI • Fluoride, R4N+ • Bisulfate, R4N+ • Hydrazine, tosyl • TsOH • DBU • CuOTf • PBu3 • O=C(OR)Cl • DMAP • NaH • Allyl-Br • OsO4 • Periodate, sodium • 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 •

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