Syntheses in the series of lycopodium alkaloids VI. Photochemical additions of vinylogous imides and methyl methacrylate

✍ Scribed by Z. Koblicová; K. Wiesner

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 210 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70348-0

✦ Synopsis

We wish to report the photochemical addition of methyl methacrylate to the compound II. We have chosen this system beoause it is very readily obtainable and can serve both as a model and actual starting material for approaches to a variety of Iycopodium alkaloids.

Compound II was obtained* from the previously described (1) compound I. Compound I was benzylated in dry benzene-dimeth,vlformamide with sodium hydride and benzyl chloride at 115'C. The yield was 90% of compound II [(C,,H,,NO,, m.p. 64-66'C.; m.w. (mass-spectrum) = 255; I.R.: 1700, 1650 1625 cm-'; U.V.: h. = 296 mu (E = 16,000)1 .* Compound II was irradiated with 4 -5 moles of methyl methacrylate in tetrahydrefuran at -7O'C. in a Pyrex container as described previously (1). Chromatography on silica gel gave a 58% yield of the two epimers III and IV in a ratio lrl. The anti-epimer III orystallized out from acetone [(C,,R,,NO,), I-P. 158'C. (suetone)! m.w. (mass-spectrum) = 355; I.R.: 1645 (laotam), 1730, 1705 cm-' (ester, ketone)! N.M.R.: singlet (3 H) * This eqeriment was performed br Dr. J. 0. MoCluekey in connection with l tker work. The compmnd II aotually used in this work wae prepared by Lizzie Poon. * Tke mass, I.B. and X.M.B. opeotra of all oerpounda have been recorded.

OmZy the mere nlevamt of the80 data are gimn to aohieve brewiity.