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Total synthesis of Akuammicine:
Reference: Bonjoch, J.; Sole, D.; Garcia-Rubio, S.; Bosch, J. J. Am. Chem. Soc. 1997, 119, 7230. DOI
Keywords: Si-Propargyl+Enone, Intram • Amine-6 • N-Me -> N-CO2R • Ketone -> Enolsilane • Ketone -> Ketone-α-SeR • Enolsilane -> Ketone-α-SePh • Reductive amination, B-H • Amine-5 • Selenoxide-Ei -> Enone-6 • Ketone -> Enone • Claisen acylation, Mander • Ketone enolate+Mander • Amine+Propargyl-I • Hydrogenation-NO2 • Aryl-NO2 -> Aryl-NH2 • Hydrogenation-Allene • Ozonolysis •
Reagents: Propargyl-Si • BF3 • LiNiPr2 • H2, Pd • O3 • NH2Me • O=C(OR)Cl • NH(SiMe3)2 (HMDS) • SiMe3-I • SePh-Cl • O3 • Propargyl-I • Carbonate, potassium • HCl • H2, Pd • O=C(OR)CN • NHiPr2 • BH3CN-Na+

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