Efficient Asymmetric Synthesis of Novel Gastrin Receptor Antagonist AG-041R via Highly Stereoselective Alkylation of Oxindole Enolates

An efficient method for asymmetric synthesis of the potent Gastrin/CCK-B receptor antagonist AG-041R was developed. Core oxindole stereochemistry was established by asymmetric alkylation of oxindole enolates with bromoacetic acid esters, using l-menthol as a chiral auxiliary. The key alkylation reac...

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Veröffentlicht in:	Journal of organic chemistry 2006-10, Vol.71 (22), p.8559-8564
Hauptverfasser:	Emura, Takashi, Esaki, Toru, Tachibana, Kazutaka, Shimizu, Makoto
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds, terpenoids, prostaglandins, steroids Alkylation Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Molecular Structure Organic chemistry Preparations and properties Receptor, Cholecystokinin B - antagonists & inhibitors Stereoisomerism Terpenoids
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Beschreibung
Zusammenfassung:	An efficient method for asymmetric synthesis of the potent Gastrin/CCK-B receptor antagonist AG-041R was developed. Core oxindole stereochemistry was established by asymmetric alkylation of oxindole enolates with bromoacetic acid esters, using l-menthol as a chiral auxiliary. The key alkylation reaction of the oxindole enolates generated tetrasubstituted chiral intermediates with high diastereoselectivity. The stereoselective alkylation reactions are described in detail.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo061541v