24204-35-1Relevant academic research and scientific papers
CONFORMATIONAL DIFFERENCE BETWEEN ERYTHRINAN- AND HOMOERYTHRINAN-3-ONES: TOTAL SYNTHESIS OF (+/-)-SCHELHAMMERIDINE AND (+/-)-3-EPISCHELHAMMERIDINE
Tsuda, Yoshisuke,Hosoi, Shinzo,Murata, Masami
, p. 311 - 316 (1990)
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.
Synthesis of homoerythrinan alkaloids of 1(2)-alkene and 1,6-diene types: Total synthesis of comosine, dihydroschelhammeridine, schelhammeridine, and 3-epischelhammeridine
Tsuda, Yoshisuke,Murata, Masami,Hosoi, Shinzo,Ikeda, Mariko,Sano, Takehiro
, p. 515 - 524 (2007/10/03)
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.
