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Tocopherol side chain synthesis via asymmetric organocatalytic transfer hydrogenation and convenient measurement of stereoselectivity
- Issue Date
- Oct-2014
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- Tocopherol; Asymmetric synthesis; Organocatalyst; Stereoselectivity; UV-HPLC
- Citation
- TETRAHEDRON LETTERS, v.55, no.43, pp.5895 - 5897
- Indexed
- SCIE
SCOPUS
- Journal Title
- TETRAHEDRON LETTERS
- Volume
- 55
- Number
- 43
- Start Page
- 5895
- End Page
- 5897
- ISSN
- 0040-4039
- Abstract
- An asymmetric synthetic route for 1-iodofarnesane, a key intermediate for tocopherol side chain synthesis, starting from (+)-(R)-citronellal was developed. 1-Iodofamesane 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 C-15 alcohol was found to be suitable to give proper polarity and UV-activity for chiral UV-HPLC analysis. (C) 2014 Elsevier Ltd. All rights reserved.
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Related Researcher
- Nam, Tae gyu
- COLLEGE OF PHARMACY (DEPARTMENT OF PHARMACY)