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A straightforward entry to the ervitsine skeleton. Synthesis of 16-demethyleneervitsine

✍ Scribed by M.-Lluisa Bennasar; Ester Zulaica; Bernat Vidal; Joan Bosch

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
262 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

Abdruc?: A short sydetic route to 16-demethyleneavidne (6). based on the nucleophilic addition of 2-actsty& in&& enolates to Kalkyl-@cylpyddinimn salts and further acid cycliition of the resulting l&dihydropydine in-s, is mported. Ervitsinel is a minor 2-acylindole alkaloid isolated in 1977 from Pandaca b&read having a rather unusual stmctum, presumably related to the alkaloids of the sarpagine group, in which the tryptamine carbon atoms (Cs-C& are in a rearranged situation with C&6 and c5<7 bonds. Other remarkable features am the presence of a seven-membered C ring included in a bridged bicyclic system and two exocyclic (16-methylene and 20ethylidene) piperidme double bonds. No synthesis for this alkaloid has been reported so far, Previous approaches to its tctracyclic hexahydro-1,5-methanoazonino[4,3-b]indole framework imply closure of C ring in the last synthetic steps by cyclization of either an iminium salt upon the indoie 3-position4 (formation of Q-C7 bond) or. a 4-piperidineacetic acid upon * %0&H,

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