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Mass spectrometry in structural and stereochemical problems tabersonine (alkaloids of Amsonia Tabernaemontana Walt.

✍ Scribed by Monique Plat; Jean Le Men; Maurice-Marie Janot; J.M. Wilson; H. Budzikiewicz; Lois J. Durham; Y. Nakagawa; Carl Djerassi

Publisher
Elsevier Science
Year
1962
Tongue
French
Weight
298 KB
Volume
3
Category
Article
ISSN
0040-4039

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✦ Synopsis

SOMETIME ago,2 there was isolated from Amsonia Tabernaemontana Walt. (fam. Aoocvnaceae) a new alkaloid, named tabersonine. The analytical data (C H 2. 24_26N202), the high rotation of the hydrochloride ([a],-310"), and especially the characteristic ultraviolet and infrared spectral properties 3 indicated the presence of the grouping I and it was assumed 394 that tabersonine was a member of the akuammicine (II)4p5 class. We should now like to report -largely on the basis of mass spectrometric measurements and new chemical evidence-that (-)-tabersonine possesses structure IVa, 6 thus la Part IX. For piper VIII see C. Djerassi, H. Budzikiewicz and J.M. Wilson, Tetrahedron Letters 263 (1962), preceding paper. lb Part III. For papers I and II see ref. 2 and 3.

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