Total synthesis of Coccinelline:
| Reference: | Stevens, R. V.; Lee, A. W. N. J. Am. Chem. Soc. 1979, 101, 7032. DOI |
| Reactions: | Reductive amination, B-H • Michael Enal • CarboxEster enolate+Enal • Enal+Enolate • ConjAdd Enolate • Claisen acylation, ester • CarboxEster enolate+CarboxEster • Wittig-methyl • Amine → AmineOxide • Hydrogenation alkene • Decarboxylation Krapcho • Decarboxylation Krapcho • Decarboxylation Krapcho • Robinson-Schoepf • Amine-6 • Mannich • Bicyclo(440)-aza • Aldehyde → Acetal(Me) • |
| Reagents: | NaOMe • HOMe (react) • Chloride, sodium • NaH • Chloride, sodium • Acetate, ammonium • BH3CN-Na+ • Chloride, sodium • PPh3=CH2 • H2, Pd • Acrolein • Malonate • DMF (solvent) • DMF (solvent) • DMF (solvent) • Acetoacetate • Perbenzoic acid, 3-chloro • |