31470-47-0Relevant articles and documents
Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization
Renner, Jonas,Thakur, Ashish,Rutz, Philipp M.,Cowley, Jacob M.,Evangelista, Judah L.,Kumar, Puneet,Prater, Matthew B.,Stolley, Ryan M.,Louie, Janis
supporting information, p. 924 - 928 (2020/02/04)
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
Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical
Chea, JongMyoung,Clive, Derrick L. J.
, p. 10294 - 10298 (2015/11/03)
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%.
A simple enantioselective route to functionalized indolizidines: Synthesis of (+)-ipalbidine and (+)-antofine
Pansare, Sunil V.,Lingampally, Rajinikanth,Dyapa, Rajendar
supporting information; experimental part, p. 2235 - 2238 (2011/06/19)
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
