First preparation of single-enantiomer juvenile hormone III acid and (R)-juvenile hormone III-d₃

Abstract

The (R)- and (S)-enantiomers of juvenile hormone (JH) III acid [(R)-2 and (S)-2] were prepared by the hydrolysis of (R)- and (S)-JH III [(R)-1 and (S)-1], respectively. Each enantiomer of 2 was purified by preparative reversed-phase high performance liquid chromatography in a single operation. (RS)-2 was methylated with CH₃I and K₂CO₃ in MeCN, yielding (RS)-1. (R)-JH III-d ₃ [(R)-3], a single-enantiomer internal standard for quantification, was prepared from (R)-2 with CD₃I and K₂CO₃ in MeCN.

Keywords:

• enantiomer
• juvenile hormone
• JH
• JH III acid
• JH III-d ₃

Acknowledgements

The authors are grateful to Ms I. Maeda (NFRI) for the NMR measurements. A.I. is grateful to Dr T. Shinoda (NIAS), Dr T. Shiotsuki (NIAS) and Dr K. Furuta (NIAS) for valuable discussions, LC–MS measurements and the use of Chiralpak columns.