104069-35-4

Upstream product

• 1242597-71-2 (S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate 
• 917-54-4 methyllithium 
• 1242597-68-7 (6R,7S,8aS)-octahydro-6-(4-methoxyphenyl)-7-methylindolizin-7-ol 
• 1301743-51-0 (6R,7S,8aS)-octahydro-6-(4-methoxyphenyl)indolizin-7-ol 
• 1301743-54-3 methyl 3-(2-((2S, 3R)-2-hydroxy-3-(4-methoxyphenyl)-4-nitrobutyl)-1,3-dioxolan-2-yl)propanoate 
• 1301743-48-5 (6S,7R)-methyl 6-hydroxy-7-(4-methoxyphenyl)-8-nitro-4-oxooctanoate 
• 1301743-49-6 (3R,4S)-4-hydroxy-6-(3-methoxy-3-oxopropyl)-3-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine-1-oxide 
• 1301743-50-9 methyl 3-((2R,4S,5S)-4-hydroxy-5-(4-methoxyphenyl)-N-hydroxypiperidin-2-yl)propanoate 
• 1301743-55-4 (6R,7S,8aS)-hexahydro-7-hydroxy-6-(4-methoxyphenyl)indolizin-3(5H)-one 
• 1242597-75-6 (6S,8aR)-6-(4-methoxyphenyl)hexahydroindolizin-7(1H)-one 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 2749-94-2 1-methoxy-4-(prop-1-yn-1-yl)benzene 

Downstream Products

• 23506-90-3 4-[(8aS)-7-methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl]phenol 

Relevant academic research and scientific papers

Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical

N-Boc (S)-proline was converted into (2S)-2-[(phenylselanyl)methyl]pyrrolidine, which was alkylated on nitrogen with 2-bromo-1-(4-methoxyphenyl)ethan-1-one. Reaction with vinyllithium, 6-exo-trig radical cyclization (Bu3SnH, AIBN, PhMe, 110 °C), dehydration (P2O5, H3PO4), and demethylation (BBr3) gave (+)-ipalbidine with ee >99%.

Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization

A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azet

A simple enantioselective route to functionalized indolizidines: Synthesis of (+)-ipalbidine and (+)-antofine

An efficient route to functionalized indolizidines from an enantiomerically enriched γ-nitro ketone is described. The nitro ketone is obtained by an organocatalytic, enantioselective ketone-nitro alkene Michael addition. Oxidative ring expansion of the ni

Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine

This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.