33023-02-8

Upstream product

• 73971-35-4 1,5,6,8a-tetrahydro-8-(1-hydroxybutyl)-3(2H)-indolizinone 
• 123-72-8 butyraldehyde 
• 109720-83-4 8-bromo-1,2,3,5,6,8a-hexahydroindolizine 
• 81943-25-1 (7R,8R,8aR)-8-Butyryl-7-chloro-hexahydro-indolizin-3-one 
• 79476-83-8 (+/-)-1,5,6,8a-tetrahydro-8-(1-oxobutyl)-3(2H)-indolizinone 
• 81957-66-6 1-((E)-5-Oxo-oct-3-enyl)-pyrrolidine-2,5-dione 
• 131251-99-5 methyl 1,2,3,5,6,8a-hexahydro-3-oxoindolizine-8-carboxylate 
• 125475-13-0 (8aS,SR)-1,2,3,5,6,7,8,8a-octahydro-8-<(4-methylphenyl)sulfinyl>indolizine 
• 125475-12-9 (-)-(S)-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>indolizine 
• 123642-79-5 (+)-(R)-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole 
• 872-32-2 2-methyl-1H-pyrroline 
• 125475-14-1 (8S,8aS,1'S,SS)-8-(1-hydroxybutyl)-1,2,3,5,6,7,8,8a-octahydro-8-<(4-methylphenyl)sulfinyl>indolizine 
• 125517-34-2 (8R,8aS,1'S,SS)-8-(1-hydroxybutyl)-1,2,3,5,6,7,8,8a-octahydro-8-<(4-methylphenyl)sulfinyl>indolizine 
• 131252-00-1 (1,2,3,5,6,8a-hexahydroindolizin-8-yl)methanol 

Relevant academic research and scientific papers

Total Sythesis of Elaeokanine A

A new general approach to synthesis of Elaeocarpus alkaloids is described which utilizes the intramolecular imino Diels-Alder reaction as the key ring-forming step.The methodology has been applied to total synthesis of the alkaloid Elaeokanine A.

α-ACYLIMINIUM ION SYNTHESIS OF ELAEOKANINE B

Elaeokanine B has been synthesized utilizing the acid-catalyzed cyclisation of hydroxylactam 9 as key step in the formation of the chloride 10.

A Practical Preparation of the Indolizidine Nucleus: Synthesis of (+/-)-Elaeokanine A

Reduction of 3 followed by acid-catalyzed cyclization provides α,β-unsaturated ester 5.As 3 can be prepared in two steps from succinimide, acrolein, and trimethyl phosphonoacetate, this is a practical method for the assembly of the indolizidine nucleus.The structure of 5 was secured by conversion to elaeokanine A, 7.

Asymmetric Total Syntheses of Elaeokanines A and B via α-Sulfinyl Ketimine

α-Lithiated (+)-(R)-4,5-dihydro-2-methyl>-3H-pyrrole (4) underwent annulation with 1,3-diiodopropane to give (-)-(S,S)-1,2,3,5,6,7-hexahydro-8-indolizine (6), which was converted into (-)-elaeokanine B (three steps) and (+)-elaeokanine A (four steps).

Synthesis of Indolizidine Alkaloids via the Intramolecular Imino Diels-Alder Reaction

An intramolecular imino Diels-Alder strategy has been developed for total synthesis of the indolizidine alkaloids δ-coniceine (1), tylophorine (2), elaeokanine A (3), and elaeokanine B (4).In all cases, an acyl imine dienophile was generated thermally in situ from a methylol acetate precursor.Diene-methylol acetate 8 has been cyclized via 10 to lactam 11, which was converted to δ-coniceine.Similarly, intermediate methylol acetate 18 was transformed via 19 and 20 to pentacyclic lactam 21, and then to tylophorine.In the syntheses of elaeokanine A and B,a masked diene precursor, in the form of a dihydrothiophene dioxide system, was prepared.Thus, compound 35 was cyclized via intermediate 23b to afford bicyclic lactams 37 and 39 in a 5:4 ratio.These products were subsequently converted to 3 and 4.

Elaeocarpus Alkaloids. The Synthesis Of (+/-)-Elaeokanine A, (+/-)-Elaeokanine B, And (+/-)-Elaeokanine C

The synthesis of (+/-)-elaeokanines A, B and C by using compound 2 as an intermediate is described.