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Synthesis of Diastereomers of 1,3-cis-25-Dihydroxy-19-norvitamin D3. 2016
Kosuke Usuda, and
Tanima Biswas, and
Takuya Yamaguchi, and
Yusuke Akagi, and
Koji Yasui, and
Motonari Uesugi, and
Isao Shimizu, and
Seijiro Hosokawa, and
Kazuo Nagasawa
Graduate School of Technology, Tokyo University of Agriculture and Technology.
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 (1)H-NMR and nuclear Overhauser effect (NOE) experiments.
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