84002-73-3Relevant academic research and scientific papers
SYMMETRIE-ENHANCED REMOTE DICARBANION ANNULATIONS FOR LATENT CYCLOALKENONES: APPLICATION TO ALKALOIDS AND TERPENES
Lansbury, Peter T.,Spagnuolo, Ciro J.,Grimm, Erich L.
, p. 3965 - 3968 (2007/10/02)
Fuctionalized 1,n-dicarbanions (n = 4,5,6) react with α,α'-methallyl dihalides to produce n+3 substituted α-methylenecycloalkanes that are synthetic equivalents of two differentiable cycloalkenones.
2-CYANO Δ3 PIPERIDEINES X1: BIOMIMETIC SYNTHESIS OF THE LADYBUG ALKALOIDS OF THE ADALINE SERIES
Gnecco Medina, D. H.,Grierson, D. S.,Husson, H.-P.
, p. 2099 - 2102 (2007/10/02)
The ladybug alkaloids 4 and 17 of the adaline series were synthesized via intramolecular Mannich reaction of the intermediate iminium-enols 13, generated from the corresponding 2-cyano-2'-alkyl-6- (propan-2-one ethylene ketal) piperidines 11 and 12.
ASYMMETRIC SYNTHESES OF THE LADYBUG ALKALOID ADALINE AND 1-METHYL-9-AZABICYCLO (3.3.1)NONAN-3-ONE
Hill, Richard K.,Renbaum, Louis A.
, p. 1959 - 1963 (2007/10/02)
The double Michael addition of benzylamine to 3-alkyl-2,7-cyclooctadienones, followed by hydrogenolysis, affords bridgehead substituted 9-azabicyclo(3.3.1)nonan-3-ones.Use of (+)-α-methylbenzylamine in the addition leads to mixtures of diastereometric adducts in unequal amounts.Although the degree of asymmetric induction is low (10-20 percent ee), the diastereomers can be easily separated, affording pure enantiomeric forms of the ladybug alkaloid adaline 1 and the Euphorbia alkaloid 3.
