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Conformational Studies of (±)-11,12-Didehydro-11-deoxycorynoline and (+)-11,13-Didehydro-11-deoxychelidonine, Hexahydrobenzo[c]phenanthridine-Type Alkaloid Derivatives, by X-Ray Crystal Structure and NMR Analyses

✍ Scribed by Miyoko Kamigauchi; Yukiko Maekawa; Chisato Tode; Yasuko In; Toshimasa Ishida


Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
253 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

The X‐ray crystal analyses of the two 11‐deoxy‐didehydrohexahydrobenzo[c]phenanthridine‐type alkaloid derivatives 3 and 4, derived from (±)‐corynoline (1) and (+)‐chelidonine (2), established their structures as (±)‐(5b__RS__,12b__RS__)‐5b,12b,13,14‐tetrahydro‐5b,13‐dimethyl[1,3]benzodioxolo[5,6‐c]‐1,3‐dioxolo[4,5‐i]phenanthridine (3) and (+)‐rel‐(12b__R__)‐7,12b,13,14‐tetrahydro‐13‐methyl[1,3]benzodioxolo[5,6‐c]‐1,3‐dioxolo[4,5‐i]phenanthridine (4). The conformations of 3 and 4 in CDCl~3~ were determined on the basis of ^1^H‐ and ^13^C‐NMR spectroscopy.