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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 • Enone+Si-R • Amine-6 • N-Me → N-C(O)OR • Ketone → EnolSilane • Ketone → Ketone-α-SeR • EnolSilane → Ketone-α-SeR • Reductive amination, B-H • Amine-5 • N-H → N-Alkyl • Selenoxide-Ei → Enone • Ketone → Enone • Claisen acylation, Mander • Ketone enolate+Mander • N-H → N-Propargyl • Nitro → Amine • Indole synthesis • Hydrogenation Allene • Ozonolysis •
Reagents: Propargyl-Si • BF3·OEt2 • LiNiPr2 • H2, Pd • O3 • NH2Me • O=C(OR)Cl • NH(SiMe3)2 (HMDS) • SiMe3-I • O3 • Propargyl-I • Carbonate, potassium • HCl • H2, Pd • O=C(OR)CN • NHiPr2 • BH3CN-Na+

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