HETEROLYTIC FRAGMENTATION OF DELTALINE, A NORDITERPENOID ALKALOID

Authors
SRIVASTAVA SK JOSHI BS NEWTON MG LEE D PELLETIER SW
Citation
Sk. Srivastava et al., HETEROLYTIC FRAGMENTATION OF DELTALINE, A NORDITERPENOID ALKALOID, Tetrahedron letters, 36(4), 1995, pp. 519-522
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
4
Year of publication
1995
Pages
519 - 522
Database
ISI
SICI code
0040-4039(1995)36:4<519:HFODAN>2.0.ZU;2-Z
Abstract
The rearrangement product obtained by treatment of the norditerpenoid alkaloid deltaline (1) with SOCl2 in moist benzene had been assigned s tructure 5. This compound was also obtained by treatment of 10-chloro- 10-deoxydeltaline (4) with aqueous MeOH. However, when (4) was treated with methanolic KOH, a novel rearranged pyrrolidine (8) was obtained. Structures 5 and 8 for these heterolytic fragmentation products were established by nmr spectroscopic data and an X-ray crystal structure d etermination of 8.