- Probing the structural requirements for vitamin D3 inhibition of the hedgehog signaling pathway
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A structure-activity relationship study to elucidate the structural basis for hedgehog (Hh) signaling inhibition by vitamin D3 (VD3) was performed. Functional and non-functional regions of VD3 and VD2 were obtained through straightforward synthetic means
- Deberardinis, Albert M.,Banerjee, Upasana,Miller, Michele,Lemieux, Steven,Hadden
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scheme or table
p. 4859 - 4863
(2012/08/13)
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- Continuous-flow synthesis of vitamin D3
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A highly efficient, two-stage, continuous-flow synthesis of vitamin D 3 from provitamin D3 was achieved. The developed method afforded the desired product in high yield (HPLC-UV: 60%, isolated: 32%) and required neither intermediate purification nor high-dilution conditions. The Royal Society of Chemistry 2010.
- Fuse, Shinichiro,Tanabe, Nobutake,Yoshida, Masahito,Yoshida, Hayato,Doi, Takayuki,Takahashi, Takashi
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scheme or table
p. 8722 - 8724
(2011/02/24)
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- A new synthetic route to 1,25-dihydroxy-vitamin D3
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A synthesis of 1,25-dihydroxy-vitamin D3 using a new acetylenic Ring-A precursor is described. Ring-A synthons 4a or 4b can be prepared in homochiral form by a diastereoselective diazoester cyclization.
- Wilson, Stephen R.,Venkatesan,Augelli-Szafran,Yasmin
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p. 2339 - 2342
(2007/10/02)
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- Biomimetic oxidation of vitamin D by iron-sulfur model cluster and dioxygen system
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Oxidation of vitamin D3 with a combination of iron-sulfur protein model cluster, (n-Bu4N)2[Fe4S4(SPh)4], and molecular oxygen produced (5E)-10-oxo-10-norvitamin D3 and 8α-hydroxy-9,10-seco-4,6,10(19)-cholestatrien-3-one, a new type of vitamin D metabolites, mimicking biological oxidation.
- Yamamoto,Imae,Yamada
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p. 4903 - 4906
(2007/10/02)
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- A General Method for the Synthesis of 3,5-Cyclovitamin D3 and Derivatives. A Stereoselective Synthesis of Vitamin D3
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A stereoselective synthesis of vitamin D3 (1) was achieved via 3,5-cyclovitamin D3 (33) which was synthesized from the chiral aldehyde (3) and the vinyl bromide (27) derived from Grundmann's ketone (25). (+/-)-(Z)-5-(2-Cyclohexylidene-ethylidene)-4-methylenecyclohexane-r-1, t-3-diol (24) as a model compound of 1α-hydroxyvitamin D3 was also stereoselectively synthesized via the solvolysis of (+/-)-α-cyclohexylidenemethyl-3β-methoxymethoxy-2-methylenebicyclohexane-1-methanol (21) which was prepared from the aldehyde (12) and the organostannane (16).
- Nemoto, Hideo,Wu, Xiao-Ming,Kurobe, Hiroshi,Minemura, Kayoko,Ihara, Masataka,at. al.
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p. 1185 - 1190
(2007/10/02)
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- A FACILE RING-OPENING REACTION OF CYCLOBUTENES: APPLICATION TO A SYNTHESIS OF VITAMIN D3
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The exraordinary accelerating effects of arylsulfinyl, arylsulfonyl, and diphenylphosphinoyl carbanion substituents for cyclobutene ring-opening reaction of bicyclo-oct-1(6)-ene derivatives are described.The scope and limitation of this new type of
- Nemoto, Hideo,Suzuki, Koji,Tsubuki, Masayoshi,Minemura, Kayoko,Fukumoto, Keiichiro,et al.
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p. 1123 - 1132
(2007/10/02)
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