Heterolytic fragmentation of deltaline, a norditerpenoid alkaloid

Srivastava, Santosh K. ; Joshi, Balawant S. ; Newton, M. Gary ; Lee, Doowon ; Pelletier, S. William (1995) Heterolytic fragmentation of deltaline, a norditerpenoid alkaloid Tetrahedron Letters, 36 (4). pp. 519-522. ISSN 0040-4039

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Related URL: http://dx.doi.org/10.1016/0040-4039(94)02300-Z


The rearrangement product obtained by treatment of the norditerpenoid alkaloid deltaline (1) with SOCl2 in moist benzene has been assigned structure 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 determination of 8.

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