Synthesis 2011(5): 708-710  
DOI: 10.1055/s-0030-1259483
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Easy Access to 9-Epimers of Cinchona Alkaloids: One-Pot Inversion by Mitsunobu Esterification-Saponification

Łukasz Sidorowicz, Jacek Skarżewski*
Department of Organic Chemistry, Faculty of Chemistry, Wrocaw University of Technology, 50-370 Wrocaw, Poland
Fax: +48(71)3284064; e-Mail: jacek.skarzewski@pwr,wroc.pl;
Further Information

Publication History

Received 22 November 2010
Publication Date:
31 January 2011 (online)

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Abstract

Cinchona alkaloids were efficiently converted into their 9-epi diastereomers. The applied one-pot procedure was based on the Mitsunobu esterification with 4-nitrobenzoic acid followed by in situ saponification of the ester. This method requires only one column chromatography, easily separating the epi-isomer from the native alkaloid and the Mitsunobu byproducts. The procedure gives higher yields and is operationally simpler than the previously used stereoselective hydrolysis of the corresponding sulfonic acid esters.