Ellipticine glycosides

Honda and team (68-70) at the Suntory Institute have reported a simple synthesis of N-2 ellipticine glycosides (e.g., 104) (Scheme 18), which have high water solubility and extraordinary antitumor activity (see Section XI). A key feature in the preparation of these quaternary glycosides is the use of cadmium carbonate, which seems to enhance the remarkable l, 2 -trans stereoselectivity of the condensation step. 

Scheme 17. Synthesis of ellipticine glycosides (99-101) by Pandit and co-workers (66,67).

Quaternary ellipticine glycosides have been prepared from per-acylated glycosyl bromides with the corresponding base, many showing... 

In vivo Activity of Ellipticine r,2 -/rani-GLYCOSiDES on LI210 Leukemia (69)... 

H-(3-Ethylindolyl)-D-xylopyranosylamine, eight H-(substituted-phenyl)pentopyranosylamines, and their M-nitroso-derivatives have been synthesized and their mutagenicities reported. The synthesis and antitumour activity of quaternary ellipticine N-glycosides is covered in Chapter 19, and the e.i.-m.s. fragmentation of per-Q-acetylated H-(4-substituted-phenyl)glycopyranosylamines in Chapter 22. 

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