Abstract
The crystal and molecular structure of the norditerpenoid alkaloid 1-epi-delphisine (5), C28H43NO8, M r 521.66, has been confirmed by as X-ray diffraction study using the SIR 88 analysis program. The alkaloid crystallizes in the space groupP21 with cell parameters:a=11.853(1)A,b=10.511(1)A,c=11.854(1)A,β=112.58(1),V=1363.61(0)A3,Z=2,Dcalc=1.27 g/cm3, λ (CuKα)=1.54184 A,μ (CuKα=7.2 cm−1,F(000)=564, temperature 23°C,R=0.052, for 2907 reflections. Ring A of 1-epi-delphisine exists in a chair conformation. By comparison, delphisine which bears a C-1α hydroxyl group, has ring A in a boat conformation stabilized by an intramolecular N----H-O hydrogen bond. Ring D of both of these alkaloids exists in a boat form. Unambiguous proton and carbon-13 nmr assignments for delphisine, 1-epi-delphisine and delphinine have been made by a detailed analysis of the DEPT, COSY, HETCOR, COLOC, DIFNOE, and selective INEPT nmr techniques.
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