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A stereoselective synthesis of indole alkaloid intermediates via N-acyliminium cyclizations

✍ Scribed by Veenstra, Siem J.; Speckamp, W. Nico

Book ID
121316685
Publisher
American Chemical Society
Year
1981
Tongue
English
Weight
255 KB
Volume
103
Category
Article
ISSN
0002-7863

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Total synthesis of (Β±)-anatoxin-a via N-
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✍ Karen H Melching; Henk Hiemstra; Wim J Klaver; W.Nico Speckamp πŸ“‚ Article πŸ“… 1986 πŸ› Elsevier Science 🌐 French βš– 254 KB

Anatoxin-a has been synthesized in 8 steps, starting from succinimide, 4-bromo-l--butene and dimethyl (2-oxopropyl)phosphonate, by employing as the key step an intramolecular reaction of an N-acyliminium precursor with an cu,&unsaturated ketone moiety, induced by saturated HCl in MeOH at -5OOC. Ana