Monatshefte fur Chemie p. 1073 - 1081 (2000)
Update date:2022-08-04
Topics:
Thiel, Jacek
Boczon, Wladyslaw
Wysocka, Waleria
The bisquinolizidine carbinolamine 17-hydroxylupanine was synthesized de novo from lupanine using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; its structure was established by NMR techniques. The equatorial position of the hydroxy group as well as the prevailing boat form of ring C were determined. As expected, the carbinolamine converted into the C17=N16 anhydronium perchlorate upon treatment with HClO4. NMR analysis of the salt revealed a conformational equilibrium within rings A and D, whereas rings B and C remain rigid.
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