- Diastereoselective synthesis of 3,5-trans-(+)-(3R,5R)-3-carbomethoxycarbapenam from 3-hydroxypyridine: Questioning the stereochemical assignment of the natural product
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An enantio- and diastereoselective synthesis of the methyl ester of 3,5-trans-(3R,5R)-carbapenam-3-carboxylic acid from 3-hydroxypyridine via (2R,5S)-trans-5-acetoxy-2-allylpiperidine has been achieved by employing the piperidine-pyrrolidine ring-contract
- Tanaka, Hideyuki,Sakagami, Hideki,Ogasawara, Kunio
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- Lipase-mediated synthesis of enantiopure N-carbobenzoxy-3-hydroxy- 1,2,3,4-tetrahydro- and N-carbobenzoxy-3-hydroxy-1,2,3,6-tetrahydropyridines from 3-hydroxypyridine
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Two isomeric chiral hydroxytetrahydropyridines, having high potential utility for the construction of a variety of chiral amine derivatives, have been prepared in both enantiomeric forms by employing lipase-mediated resolution starting from 3-hydroxypyridine. Thus, on exposure to sodium borohydride in the presence of carbobenzoxy chloride, 3-hydroxypyridine has been found to furnish racemic N-carbobenzoxy-3-hydroxy-1,2,3,4- tetrahydropyridine, which is resolved under trans-esterification conditions in the presence of lipase PS to give both enantiomeric products in enantiopure forms. Isomerization of the chiral 1,2,3,4-tetrahydro-product into the chiral 1,2,3,6-tetrahydro-derivative has been accomplished without loss of the original chiral integrity. The racemic 1,2,3,6-tetrahydro- derivative has also been resolved under the same lipase-mediated trans- esterification conditions.
- Sakagami, Hideki,Ogasawara, Kunio
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p. 521 - 524
(2007/10/03)
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- A Facile Synthesis of (R)-4-Amino-3-hydroxybutanoic Acid (GABOB) from 3-Hydroxypyridine
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(R)-4-Amino-3-hydroxybutanoic acid (GABOB) has been synthesized facilely from 3-hydroxypyridine via 1-carbobenzoxy-1,2,3,4-tetrahydro-3-hydroxypyridine employing lipase-mediated kinetic resolution.
- Sakagami, Hideki,Kamikubo, Takashi,Ogasawara, Kunio
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p. 221 - 222
(2007/10/03)
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