81623-85-0Relevant academic research and scientific papers
Synthesis of pyranotropanes via enantioselective deprotonation strategy
Majewski, Marek,Lazny, Ryszard
, p. 3653 - 3656 (1994)
Synthesis of tropane alkaloids darlingine, chalcostrobamine and isobellendine both in the racemic form and as unnatural enantiomers is described. Enantiomselective deprotonation of tropinone, which proceeded with ca 90% ee, was the key step in each of the syntheses. Enantioselectivity was increased in the presence of LiCl.
Synthesis of tropane alkaloids via enantioselective deprotonation of tropinone
Majewski,Lazny
, p. 5825 - 5830 (2007/10/03)
Enantioselective deprotonation of tropinone 2 with chiral lithium amides 5a and 6a, in the presence of LiCl, gave tropinone lithium enolate in up to 95% ee. The C2 symmetrical lithium amide 6a worked best when it was generated in situ from the hydrochloride salt of the corresponding amine 6b. The deprotonation was used as the key step in synthesis of tropane alkaloids:ent-anhydroecgonine, ent-knightinol, KD-B, chalcostrobamine, ent-isobellendine, and ent-darlingine. The absolute configuration of natural benzyltropane and pyranotropane alkaloids was established (by correlation with anhydroecgonine) to be 'cocaine-like' i.e., the side chain originates at C-2 of the tropane ring system in all cases.
UNE SYNTHESE EFFICACE ET RAPIDE DE L'ISOBELLENDINE, ALCALOIDE γ-PYRANOTROPANIQUE DE BELLENDENA MONTANA
Lounasmaa, Mauri,Langenskioeld, Tord,Holmberg, Carl
, p. 5179 - 5180 (2007/10/02)
An effective two step synthesis of isobellendine, starting from tropinone, is described.
