TY - JOUR
T1 - Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3
AU - Usuda, Kosuke
AU - Biswas, Tanima
AU - Yamaguchi, Takuya
AU - Akagi, Yusuke
AU - Yasui, Koji
AU - Uesugi, Motonari
AU - Shimizu, Isao
AU - Hosokawa, Seijiro
AU - Nagasawa, Kazuo
N1 - Publisher Copyright:
© 2016 The Pharmaceutical Society of Japan.
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
KW - 19-Norvitamin D
KW - Julia-Kocienski coupling
KW - cis-A ring synthon
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U2 - 10.1248/cpb.c16-00311
DO - 10.1248/cpb.c16-00311
M3 - Article
C2 - 27477659
AN - SCOPUS:84982746757
SN - 0009-2363
VL - 64
SP - 1190
EP - 1195
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 8
ER -