Synthesis

Stereoselective Synthesis of Aporphine Alkaloids Using a Hypervalent Iodine (III) Reagent-Promoted Oxidative Nonphenolic Biaryl Coupling Reaction. Total Synthesis …

E Anakabe, L Carrillo, D Badía, JL Vicario…

Index: Anakabe, Eneritz; Carrillo, Luisa; Badia, Dolores; Vicario, Jose L.; Villegas, Maite Synthesis, 2004 , # 7 p. 1093 - 1101

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Citation Number: 10

Abstract

Abstract The aporphine alkaloid (+)-glaucine (8a) and two other analogues 8b, c have been synthesized in good yield and high ee from the appropriate 1, 2-diarylethylamine derivatives, which were in turn prepared using (S)-(+)-phenylglycinol as chiral support. Next, a sequence of simple transformations: N-alkylation with bromoacetaldehyde diethyl acetal, N-methylation, Pommeranz-Fritsch cyclization, and ionic hydrogenation led to the key ...