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Synthesis of optically pure pyrroloquinolones via Pictet–Spengler and Winterfeldt reactions

✍ Scribed by Weiqin Jiang; Zhihua Sui; Xin Chen

Book ID: 104252324
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 256 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02147-0

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✦ Synopsis

Diastereomers of substituted 2,3,4,9-tetrahydro-1H-b-carbolines were synthesized via asymmetric Pictet-Spengler reaction of the chiral tryptamine derived from R-1-naphthalen-1-yl-ethylamine with 67% of d.e. The S,R-b-carboline can be converted to the R,R form by treating with TFA. Optically pure pyrroloquinolones were obtained from Winterfeldt oxidation of the b-carbolines without epimerization.

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