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ChemInform Abstract: A Caveat in the Application of the Exciton Chirality Method to N,N-Dialkyl Amides. Synthesis and Structural Revision of AT2433-B1.

✍ Scribed by John D. Chisholm; Jerzy Golik; Bala Krishnan; James A. Matson; David L. Van Vranken

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199935265

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✦ Synopsis

A Caveat in the Application of the Exciton Chirality Method to N,N-Dialkyl Amides. Synthesis and Structural Revision of AT2433-B1.

-During total synthesis of the antitumor antibiotic AT2433-B1 (IV) puzzling results of CD measurements are observed: while compound (Va) correctly exhibits negative chirality the methylated analogue (Vb) exhibits positive chirality. Based on these studies the absolute configuration of the amino sugar moiety of title compound (IV) is reassigned to be (3S,4S). The present work demonstrates the need for caution when N,N-dialkylamides are used in determination of absolute configuration of amino alcohols by means of exciton chirality. -(CHISHOLM,

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