Journal of Organic Chemistry p. 2274 - 2278 (1988)
Update date:2022-07-29
Topics:
Spitzner, Dietrich
Zaubitzer, Thomas
Shi, Yau-Jun
Wenkert, Ernest
Interaction of methyl N-tryptophylnicotinate bromide with the lithium salt of ethyl α-(trimethylsilyl)acetate and acid-catalyzed cyclization has yielded a tetracyclic ester, whose condensation with acetaldehyde has produced ethyl vallesiachotamate.Reactions of lithiated, alkylthiolated esters with the nicotinate salt (followed by cyclization) have afforded related adducts.Ester-to-aldehyde group conversion has to the alkaloid vallesiachotamine in the 19Z and 19E forms.
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