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Total synthesis of Dragmacidin F:
Reference: Garg, N. K.; Caspi, D. D.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 9552–9553. DOI
Keywords: Alkyl-OH → Ketone-α-OR • Li/Br → Li-Aryl • Alkyl-OH → Ketone • Ketone → Oxime • O-H → O-SO2R • Neber rearrangement • Ketone → Ketone-α-NR2 • O-Me → O-H • Pd-Heck coupling • Wittig-methyl • Allyl-OR → Allyl-H • CarboxAcid → CarboxAmide(Weinreb) • Li-Aryl+CarboxAmide • CarboxAmide(Weinreb)+Li-R • Hydrogenation Alkene • Aryl-H → Aryl-Br • Aryl-Br → Aryl-BR2 • Pd/B-Aryl+Aryl-X • Suzuki coupling • Imidazole synthesis • O-H → O-Me • Williamson etherification •
Reagents: Cr2O7·2PyH (PDC) • PPh3=CH2 • H2, Pd • NMe(OMe)-H • Carbodiimide • Pd(OAc)2 • DMSO (solvent) • H2, Pd • NaH • NBS • BuLi(n) • Pd(PPh3)4 • Carbonate, sodium • LiBF4 • Dess-Martin • NH2OH • TsCl • Bromide, R4N+ • Hydroxide, potassium • HCl • SiMe3-I • Hydroxide, sodium • MeI •

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