PROCESS FOR PRODUCING HALF-SYNTHETIC GLYCOLALKALOIDS WITH INDOLE SKELETON, PARTICULARLY NEW N UNDER B-SUBSTITUTED VINCOSIDES AND N UNDER B-SUBSTITUTED STRICTOSIDINES

摘要

Semi-synthetic gluco-alkaloids of indole structure (I) and in partic Nb substd. special classes of these i.e. vincosides and strychtosidines are prepd. from substd. tryptamines of formula (II) and secologamine derivs of formula (III). In formula (I) R=H or acyl; R3-CO where R3 is an alkyl gp. (1-4C); R1=alkyl, alkenyl, aralkyl (1-5C), opt. the benzene ring is substd. by a halogen atom, nitro- alkoxy- or alkylamino-gp. R1 may be acyl gp. of formula R4-CO, where R4 is an alkyl-, aralkyl-, alkoxy or aralkyoxy- gp. (of 1-4C); 'O' in the tryptamine formula (II) is or an alkyl-aralkyl gp (1-5C); opt. the benzene ring is substd by a halogen atom, nitro-, alkoxy-, or arylamino- gps. R2 as in (I) In formula (III) of secologamine derivs., R=H or an acyl gp. of formula R3-CO where R3 as in (I). (a) In the prepn of Nb substd vincosides fo formula (1a) being a specific variant of (1), 'O' in cpd. (II) and R in cpd (III) are other than hydrogen. Prepn of cpd. (1a) is carried out in a nonpolar aprotic solvent, pref. benzene. The extracted prod. is opt. de-acylate. (b) Strychtosidines of formula (IV) are obtd. during the prepn of Nb substd strychtosidines of general formula (1b) a specific subgroup of cpds. (I). Cpds (IV) react with cpds R4-X (V) in the presence of a base of a greater conc. than a two-molar excess. Opt the end prod. is acylated.