A rigorous proof of the selegaine structure

✍ Scribed by H. Yoshimura; Z. Valenta; K. Wiesner

• Book ID: 104249802
• Publisher: Elsevier Science
• Year: 1960
• Tongue: French
• Weight: 172 KB
• Volume: 1
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99306-2

✦ Synopsis

THE elucidation of the structure of annotinine, the alkaloid of Lycopodium annotinum 2 , revealed for the first time the structural type to be expecte.d in other ucopodium alkaloids. The key factor in the deduction of this structure was the identification of dehydrogenation products, and extensive systematic degradation3, Since then, structures have been proposed for additional alkaloids of this type, namely, lycopodine 4 , selagine 5 and the obscurines". Extensive use of N.M.R. spectroscopy6, dehydrogenation4,' ' N.R.C. postdoctoral fellow on leave from Qushu University, Japan. 2 K. Wiesner Z. Valenta W.A. Ayer and C. Bankiewicm, Chem. and fnd. 1019 (1456); K. Wiesner, W.A. Ayer, L.R. Fowler and Z. Valenta Chem. and Ind. 564 (1957); K. Wiesner, Z. Vaienta W Fcwler and J.E. Francis, Tetrah~dr~~~~~~,(1L~~~). 3 A complete X-ray analysis (M. tizybylska and P.R. Ahmed, Acts Cryst. ll, 718 (1958)) corroborated the the proposed structure.