By R.H.F Manske, H.L. Holmes
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Extra resources for Alkaloids: Chemistry and Pharmacology, Volume 14
Buxitrienine-C. Buxitrienine-C (162) was found in Buxus madagascarica subsp. xerophila, forma salicicola (79). It is the first representative of Buxus alkaloids possessing a conjugated triene in positions C- 1-C-2, C-1O-C- 19, and C-9-C- 11. The structural formula of buxitrienine-C was inferred on the basis of its UV, IR, PMR, and mass spectral data; starting from cycloxobuxidine-F (79), the partial synthesis was intended to confirm this assumption. 162 c. Cyclomicrosine-C. Cyclomicrosine-C (163) was found in Buxus microphylla var.
The PMR spectrum of veracintine showed two singlets, indicating 1. STEROID ALKALOIDS 31 C-18 and C-19 angular methyl groups of a normal steroid ring system with a C-5 double bond, one doublet corresponding to a secondary methyl group a t C-20, signals of a C-6 vinyl, and a C-22 proton. 1 ppm suggested a C-26 methyl group in the neighborhood of the double bond. The base peak in the mass spectrum a t m/e 82 was advanced for a pyrroline ring resulting from the C-20 and C-22 bond fission. The IR spectrum indicated the presence of a hydroxy group and an azomethine double bond.
The negative molecular rotation increment of compound 152 after acetylation confirmed the a-orientation of the C-16 hydroxy group. Dihydrocyclokoreanine-A (152) and cyclovirobuxine-A (155) have different melting points although their PMR and I R spectra differ in minor points only. Therefore it was assumed that the difference between them was due to the opposite orientation of the C-3 dimethylamino group. As the orientation of the dimethylamino group at C-3 in cyclovirobuxine-A (155) has been proved to be @equatorial, that of 38 J.