By R.H.F Manske, H.L. Holmes
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Extra info for Alkaloids: Chemistry and Pharmacology, Volume 14
8. 7" in chloroform) were shown not to be identical (78) (cf. Volume X, pp. 198, 217). 9. 2" in chloroform) revealed absorption of a hydroxyl, a n ester group, and a double bond (69). 111. Structures and Chemical and Physicochemical Properties of Buxus alkaloids A. DIBASICBuxus ALKALOIDS 1. Subgroup A a. Buxamine-A. Buxamine-A (139) isolated from Buxus madagascarica subsp. xerophilla, forma salicicola showed in its UV spectrum bands indicative of a conjugated trans diene (79). )I n its PMR specTABLE I1 Buxus ALKALOIDS Compound Molecular formula Alkaloid-E Buxaltine-H Buxamine-A Buxamine-E Buxaminol-E Buxandonine-L Buxandrine-F Buxanine-M Buxarine-E' Buxazidine-B Buxazine Hnxene-0 Buxeridine-C Buxidienine-B Buxidine-B ~~~~~~~~~ ~ Buxiramine-D Buxitrienine-C Bnxocyclamine-A Buxpiine-K ( = cyclomicrobnxine) C32H43N02 C33H48N203 Cz7H4eNaOa CzsH4eNzoz Compound No.
15 STEROID ALKALOIDS Reduction of the dione 64 with sodium borohydride gave two compounds; one of them was identified as N-benzoyl-5a,6-dihydroveratramine (65). Compound 65 was further converted into the dibenzoyl derivative 66 which on oxidation afforded the 3-0x0 compound 67. The product 67 was transformed by a known reaction sequence into (33). veratramine [ (22S,25S)-veratra-5,12,14,16-tetraenine-3/3,23/3-diol] Masamune and associates ( 4 9 ) converted the ketone 59 into the two epimeric C-20 bromides 68.
Optical rotations were measured in chloroform unless stated otherwise. 34 J. TOMKO AND z. V O T I C K ~ trum, signals attributable to four tertiary methyls, one secondary methyl, two dimethylamino groupings, and two olefinic protons were apparent. The mass spectrum of 139 was characteristic of both dimethylamino groupings a t C-3 and C-20. Although buxamine-E (140) has already been described (c.. Vol. I X , p. 405) no correlation between the two alkaloids has been made in order to confirm the structure of 139.
Alkaloids: Chemistry and Pharmacology, Volume 14 by R.H.F Manske, H.L. Holmes