Synthesis of Diastereomers of 1,3-cis-25-Dihydroxy-19-norvitamin D3

Kosuke Usuda; Tanima Biswas; Takuya Yamaguchi; Yusuke Akagi; Koji Yasui; Motonari Uesugi; Isao Shimizu; Seijiro Hosokawa; Kazuo Nagasawa

doi:10.1248/cpb.c16-00311

Regular Articles

Synthesis of Diastereomers of 1,3-cis-25-Dihydroxy-19-norvitamin D₃

Kosuke Usuda, Tanima Biswas, Takuya Yamaguchi, Yusuke Akagi, Koji Yasui, Motonari Uesugi, Isao Shimizu, Seijiro Hosokawa, Kazuo Nagasawa

Author information

Kosuke Usuda
Graduate School of Technology, Tokyo University of Agriculture and Technology
Tanima Biswas
Faculty of Science and Technology, Waseda University
Takuya Yamaguchi
Graduate School of Technology, Tokyo University of Agriculture and Technology
Yusuke Akagi
Graduate School of Technology, Tokyo University of Agriculture and Technology
Koji Yasui
Graduate School of Technology, Tokyo University of Agriculture and Technology
Motonari Uesugi
Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University
Institute for Chemical Research, Kyoto University
Isao Shimizu
Faculty of Science and Technology, Waseda University
Seijiro Hosokawa
Faculty of Science and Technology, Waseda University
Kazuo Nagasawa Corresponding author
Graduate School of Technology, Tokyo University of Agriculture and Technology

Keywords: 19-norvitamin D₃, cis-A ring synthon, Julia–Kocienski coupling

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2016 Volume 64 Issue 8 Pages 1190-1195

DOI https://doi.org/10.1248/cpb.c16-00311

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Abstract

1β,3β,25-Dihydroxy-19-norvitamin D₃ (4a) and 1α,3α,25-dihydroxy-19-norvitamin D₃ (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(−)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia–Kocienski olefination to construct the diene unit. The structures of the products were confirmed by ¹H-NMR and nuclear Overhauser effect (NOE) experiments.

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