title: Synthesis of Diastereomers of 1,3-cis-25-Dihydroxy-19-norvitamin D3.
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 (1)H-NMR and nuclear Overhauser effect (NOE) experiments.
authors.affiliation: Graduate School of Technology, Tokyo University of Agriculture and Technology.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Usuda
authors.forename: Tanima
authors.initials: T
authors.lastname: Biswas
authors.forename: Takuya
authors.initials: T
authors.lastname: Yamaguchi
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Akagi
authors.forename: Koji
authors.initials: K
authors.lastname: Yasui
authors.forename: Motonari
authors.initials: M
authors.lastname: Uesugi
authors.forename: Isao
authors.initials: I
authors.lastname: Shimizu
authors.forename: Seijiro
authors.initials: S
authors.lastname: Hosokawa
authors.forename: Kazuo
authors.initials: K
authors.lastname: Nagasawa
mesh_terms: D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011801:Quinic Acid / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011801:Quinic Acid; C083610:1,25-dihydroxy-19-norvitamin D3; D002117:Calcitriol