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Usage

Uses

Used in Pharmaceutical Industry:
Isobellendine is used as a pharmaceutical compound for its potential medicinal properties. Its alkaloid nature suggests it may have bioactive capabilities that can be harnessed for therapeutic applications, although specific uses would require further research and development.
Used in Chemical Research:
Isobellendine serves as a subject of interest in chemical research, particularly for studying the structure and properties of alkaloids. Its unique structure may provide insights into the development of new chemical compounds and contribute to the broader understanding of alkaloid chemistry.

Upstream product

• 532-24-1 tropinone 
• 51042-79-6 3-ethoxycrotonyl chloride 
• 532-24-1 tropinone 
• 167415-18-1 3-bromo-2-oxopent-3-enonitrile 
• 674-82-8 4-methyleneoxetan-2-one 
• 59272-78-5 3-morpholin-4-yl-trop-2-ene 

Relevant academic research and scientific papers

Synthesis of tropane alkaloids via enantioselective deprotonation of tropinone

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.

Synthesis of pyranotropanes via enantioselective deprotonation strategy

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.

UNE SYNTHESE EFFICACE ET RAPIDE DE L'ISOBELLENDINE, ALCALOIDE γ-PYRANOTROPANIQUE DE BELLENDENA MONTANA

An effective two step synthesis of isobellendine, starting from tropinone, is described.