129112-79-4

Upstream product

• 24204-40-8 8-oxo-3-epischelhammeridine 
• 24204-40-8 (+/-)-8-oxoschelhammeridine 
• 129112-85-2 C₁₈H₁₉NO₄ 
• 176316-54-4 C₂₀H₂₁NO₆ 
• 102487-85-4 6β-ethoxycarbonyl-7α-hydroxy-16,17-methylenedioxy-2,8-dioxo-Δ³-cis-homoerythrinan 
• 102487-86-5 6β-ethoxycarbonyl-7α-hydroxy-16,17-methylenedioxy-2,8-dioxo-cis-homoerythrinan 
• 102487-71-8 C₁₇H₁₅NO₆ 
• 102487-70-7 ethyl 2-(2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-2-benzazepin-1-ylidene)acetate 
• 102487-69-4 2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-2-benzodiazepine-1-thione 
• 129112-89-6 C₂₅H₂₅NO₄Se 
• 129112-88-5 C₁₉H₂₁NO₄ 
• 129112-80-7 16,17-methylenedioxy-3,8-dioxo-Δ¹-cis-homoerythrinan 
• 129112-85-2 C₁₈H₁₉NO₄ 
• 129112-89-6 C₂₅H₂₅NO₄Se 

Relevant academic research and scientific papers

Synthesis of homoerythrinan alkaloids of 1(2)-alkene and 1,6-diene types: Total synthesis of comosine, dihydroschelhammeridine, schelhammeridine, and 3-epischelhammeridine

Total syntheses of homoerythrinan alkaloids of 1(2)-alkene type, dihydroschelhammeridine and comosine, and those of 1,6-dienoid type, schelhammeridine and 3-epischelhammeridine, were achieved. Total synthesis of the former alkaloids provided definite proof of their A/B-cis stereochemistry. In relation to the stereochemistry, the conformations of erythrinan and homoerythrinan alkaloids are discussed.

CONFORMATIONAL DIFFERENCE BETWEEN ERYTHRINAN- AND HOMOERYTHRINAN-3-ONES: TOTAL SYNTHESIS OF (+/-)-SCHELHAMMERIDINE AND (+/-)-3-EPISCHELHAMMERIDINE

Erythrinan- and homoerythrinan-3-ones behave differently toward hydride reductions suggesting their conformational difference: for example, Δ1-erythrinan-3-one gives 3α-alcohol and Δ1-homoerythrinan-3-one gives 3β-alcohol stereoselectively on reduction with NaBH4-CeCl3 in methanol.Based on these observations, total syntheses of homoerythrinan alkaloids, schelhammeridine and 3-epischelhammeridine, and an erythrinan alkaloid, 8-oxoerysotrine, were accomplished.