Synthesis of Vallesiachotamine

DOI: 10.1021/jo00245a027

Source and publish data:

Journal of Organic Chemistry p. 2274 - 2278 (1988)

Update date:2022-07-29

Topics:

Authors:

Spitzner, Dietrich

Zaubitzer, Thomas

Shi, Yau-Jun

Wenkert, Ernest

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Article abstract of DOI:10.1021/jo00245a027

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.

Full text of DOI:10.1021/jo00245a027

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