- A General Synthetic Route to A-Ring Hydroxylated Vitamin D Analogs from Pentoses
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The enyne needed for coupling to a CD-ring fragment, namely, 3S,5R-oct-1-en-7-yne-3,5-diol, in the Trost-Dumas carbopalladation route to 1α,25-dihydroxyvitamin D3 was synthesized from D-xylose in 13 steps and 21percent yield.
- Moriarty, Robert M.,Kim, Joonggon,Brumer, Harry
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- A chiron approach to the total synthesis of (+)-aculeatin D
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(Chemical Equation Presented) A synthesis of natural aculeatin D has been achieved, with the key stereogenic centers taken from inexpensive and readily available D-xylose. In elaboration of D-xylose into a desired form readily applicable in synthesis a pr
- Zhen, Zhi-Bin,Gao, Jian,Wu, Yikang
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scheme or table
p. 7310 - 7316
(2009/05/09)
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- Synthesis of two novel chiral building blocks for anti- And syn-1,3-diols
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Two novel chiral building blocks 1 and 2 for anti- and syn-1,3-diols have been synthesized starting from the readily available and inexpensive D-(+)-xylose.
- Wu, Yong,Guan, Mei
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p. 844 - 846
(2007/10/03)
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- Preparation of 3-Deoxy-aldonolactones by Hydrogenolysis of Acetylated Aldonolactones
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Acetylated aldono-1,4-lactones, when treated with hydrogen in the presence of triethylamine and palladium on carbon, form acetylated 3-deoxy-aldono-1,4-lactones in high yield through elimination of the 3-acetoxy group and subsequent stereospecific hydrogenation of the unsaturated intermediate.Thus, acetylated D-galactono-1,4-lactone (1) yields tri-O-acetyl-3-deoxy-D-xylo-hexono-1,4-lactone (3a).Acetylated D-mannono- or D-glucono-1,4-lactone both give 3-deoxy-D-arabino-hexono-1,4-lactone (10a), whereas the four acetylated D-pentono-1,4-lactones (14-17) all afford di-O-acetyl-D-threo-pentono-1,4-lactone (18a).D-Gluconolactone can be converted into (R)-γ-caprolactone (27) on treatment with hydrogen bromide followed by a series of reductions.Similarly, D-lyxonolactone produces 2,3-dideoxy-D-glycero-pentono-1,4-lactone (29).
- Bock, Klaus,Lundt, Inge,Pedersen, Christian
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p. 155 - 162
(2007/10/02)
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