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

Article abstract of DOI:10.3987/COM-89-S49

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.