Tocopherol side chain synthesis via asymmetric organocatalytic transfer hydrogenation and convenient measurement of stereoselectivity |
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Authors: | Hyunji Lee You-Kyoung Lee Dong-Guk Kim Mi-Sun Son Tae-gyu Nam Byeong-Seon Jeong |
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Institution: | 1. College of Pharmacy and Institute for Drug Research, Yeungnam University, Gyeongsan 712-749, Republic of Korea;2. Department of Pharmacy and Institute of Pharmaceutical Science and Technology, Hanyang University, Ansan 426-791, Republic of Korea |
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Abstract: | An asymmetric synthetic route for 1-iodofarnesane, a key intermediate for tocopherol side chain synthesis, starting from (+)-(R)-citronellal was developed. 1-Iodofarnesane was prepared through eight steps in about 50% overall yield, and asymmetric transfer hydrogenation of the enal with a chiral organocatalyst was conducted as a stereoinduction step. To measure the stereoinduction level and optical purity of the product, a convenient analytical method was developed in which a phenylcarbamate derivative of the C15 alcohol was found to be suitable to give proper polarity and UV-activity for chiral UV-HPLC analysis. |
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Keywords: | Tocopherol Asymmetric synthesis Organocatalyst Stereoselectivity UV-HPLC |
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