Thalictrum alkaloids VI: (−)-Veronamine, a glycosidic benzylisoquinoline

✍ Scribed by Maurice Shamma; Michael G. Kelly; M.A. Podczasy Sr.

• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 159 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88855-9

✦ Synopsis

We wish to report the isolation, structural elucidation and synthesis of the new alkaloid (-)-veronamine (1) obtained from x. fendleri Bngelm. To our knowledge, this is the first synthesis of a glycosidlc lsoquinoline alkaloid to have been carried out.

2

Column chromatography over cellulose powder of the crude tertiary alkaloid hydrochloride salts using methyl ethyl ketone-water as eluant gave as a middle fraction an 011 which was further purified by preparative TLC over silica gel. 193 Amorphous (-)-veronamine (I) so obtained showed a very weak parent peak at m/e 489 for Cz6Hg50gN. a base peak at m/e 236, and a small but important peak at m/e 342: H3 3 rnA 236 The UV spectrum exhibited x ,":T 275 and 282 mjl (log e 3.44 and 3.43). The NMR spectrum in CDClg showed as distinct peaks a C-methyl doublet at S 1.21 (J = 6.5 Hz), a singlet N-methyl group at S 2.49, and three O-methyl groups (9 protons) as a singlet at S 3.85. Additionally, 3 m/e 342 4951 4954 No.56