Summary.
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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Received March 13, 2000. Accepted March 21, 2000
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Thiel, J., Boczoń, W. & Wysocka, W. A Stereostructural Study of 17-Hydroxylupanine and its Perchlorate. Monatshefte für Chemie 131, 1073–1081 (2000). https://doi.org/10.1007/s007060070040
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DOI: https://doi.org/10.1007/s007060070040