50412-52-7Relevant academic research and scientific papers
Biomimetic Organocatalytic Approach to 4-Arylquinolizidine Alkaloids and Application in the Synthesis of (-)-Lasubine II and (+)-Subcosine II
Virk, Seerat,Pansare, Sunil V.
, p. 5524 - 5528 (2019/07/08)
An enantioselective, biomimetic organocatalytic synthesis of 4-arylquinolizidin-2-ones, key intermediates in the synthesis of several Lythraceae alkaloids, was developed. The methodology features S-proline-mediated Mannich/aza-Michael reactions of readily available arylideneacetones and Δ1-piperideine. The total syntheses of (-)-lasubine II and (+)-subcosine II as well as the formal syntheses of structurally related Lythraceae alkaloids were achieved. The use of Δ1-pyrroline in the Mannich/aza-Michael reaction provides enantiomerically enriched 5-arylindolizidin-7-ones, which are precursors to nonopiate antinociceptive agents.
Total synthesis of (±)-Vertine with Z-selective RCM as a key step
Chausset-Boissarie, Laetitia,Arvai, Roman,Cumming, Graham R.,Besnard, Celine,Kuendig, E. Peter
supporting information; experimental part, p. 6264 - 6266 (2010/10/19)
A concise total synthesis of the strained pentacyclic alkaloid (±)-Vertine has been achieved in eleven steps with the key steps being pelletierine condensation, Suzuki-Miyaura coupling, and ring-closing metathesis.
