Heterolytic fragmentation of deltaline, a norditerpenoid alkaloid

作者: Santosh K. Srivastava , Balawant S. Joshi , M.Gary Newton , Doowon Lee , S.William Pelletier

DOI: 10.1016/0040-4039(94)02300-Z

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摘要: Abstract The rearrangement product obtained by treatment of the norditerpenoid alkaloid deltaline ( 1 ) with SOCl 2 in moist benzene has been assigned structure 5 . This compound was also 10-chloro-10-deoxydeltaline 4 aqueous MeOH. However, when treated methanolic KOH, a novel rearranged pyrrolidine 8 obtained. Structures and for these heterolytic fragmentation products were established nmr spectroscopic data an X-ray crystal determination

参考文章(10)
W. Klyne, V. Prelog, Description of steric relationships across single bonds Cellular and Molecular Life Sciences. ,vol. 16, pp. 521- 523 ,(1960) , 10.1007/BF02158433
C. A. Grob, Mechanisms and Stereochemistry of Heterolytic Fragmentation Angewandte Chemie International Edition in English. ,vol. 8, pp. 535- 546 ,(1969) , 10.1002/ANIE.196905351
Manfred E. Wolff, Cyclization of N-Halogenated Amines (The Hofmann-Löffler Reaction). Chemical Reviews. ,vol. 63, pp. 55- 64 ,(1963) , 10.1021/CR60221A004
Georg Wittig, Hans-Dieter Frommeld, Über gezielte Aldolkondensationen Chemische Berichte. ,vol. 97, pp. 3548- 3559 ,(1964) , 10.1002/CBER.19640971242
Palaniappan Kulanthaivel, S.William Pelletier, Deoxygenation reactions of c19-diterpenoid alkaloids Tetrahedron. ,vol. 44, pp. 4313- 4320 ,(1988) , 10.1016/S0040-4020(01)86133-0
M. F. Bartlett, D. F. Dickel, W. I. Taylor, The Alkaloids of Tabernanthe iboga. Part IV.1The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine Journal of the American Chemical Society. ,vol. 80, pp. 126- 136 ,(1958) , 10.1021/JA01534A036
Marvin Carmack, James P. Ferris, John Harvey, Phyllis L. Magat, Eric W. Martin, Dana W. Mayo, THE STRUCTURAL RELATIONSHIP OF DELTALINE, DELPHELINE AND LYCOCTONINE1 Journal of the American Chemical Society. ,vol. 80, pp. 497- 497 ,(1958) , 10.1021/JA01535A061
C. A. Grob, P. W. Schiess, Heterolytic Fragmentation. A Class of Organic Reactions Angewandte Chemie. ,vol. 6, pp. 1- 15 ,(1967) , 10.1002/ANIE.196700011