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Oxime ethers as potential juvenoids: Synthesis of optical isomers

✍ Scribed by Wimmer, Zdenêk ;Vašíčková, Soňa ;Šaman, David ;Romaňuk, Miroslav

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
659 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Two racemic juvenoids 5 and 6 and their optical isomers 10, 11, 17 and 18 having chiral centres in the aliphatic side chain were synthetized. The second chiral centre in the molecules remained racemic in all derivatives prepared. The absolute configurations of the optically active centres of the enantiomers were determined on the basis of the ^1^H‐NMR spectral evaluation of the diastereoisomeric MTPA esters 12, 13, 19 and 20 derived from the intermediate alcohols 8 and 15. The optical purity was established by an HPLC analysis of the corresponding MTPA esters. The ^1^H‐NMR spectra of all compounds as well as the CD spectra of all chiral isomers were measured and discussed.

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