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Conformationally Restricted Nonchiral Pipecolic Acid Analogues
The Journal of Organic Chemistry, 2009Practical syntheses of 2-azabicyclo[3.1.1]heptane-1-carboxylic (2,4-methanopipecolic), 2-azabicyclo[2.2.2]octane-1-carboxylic (2,5-ethanopipecolic), and 9-azabicyclo[3.3.1]nonane-1-carboxylic (2,6-propanopipecolic) acids are reported. The synthetic schemes are short (five, seven, and five steps, respectively) and result in reasonably high yields of the
Dmytro S, Radchenko +3 more
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1971
Publisher Summary This chapter focuses on Pipecolic Acid. A survey of the ninhydrin-positive components of the nonprotein nitrogen fraction of plants revealed several unknowns, one of which, present in the fruit of beans and other legumes, and in lesser quantities in other plants, was subsequently isolated and identified as L(–)- pipecolic acid (I ...
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Publisher Summary This chapter focuses on Pipecolic Acid. A survey of the ninhydrin-positive components of the nonprotein nitrogen fraction of plants revealed several unknowns, one of which, present in the fruit of beans and other legumes, and in lesser quantities in other plants, was subsequently isolated and identified as L(–)- pipecolic acid (I ...
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Archiv der Pharmazie, 1992
AbstractThe Diels‐Alder product 1 is transformed by Noyori reaction and catalytic hydrogenation to 4. Hydrolysis with concomitant decarboxylation of 4 furnishes the trans configuration amino acid 5. Functional group transformation (reduction, lactonization) of 5 provides 7, ring opening affords the pipecolic acid derivative 9.
Claus Herdeis, Wolfram Engel
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AbstractThe Diels‐Alder product 1 is transformed by Noyori reaction and catalytic hydrogenation to 4. Hydrolysis with concomitant decarboxylation of 4 furnishes the trans configuration amino acid 5. Functional group transformation (reduction, lactonization) of 5 provides 7, ring opening affords the pipecolic acid derivative 9.
Claus Herdeis, Wolfram Engel
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Pipecolic acid receptors in rat cerebral cortex
Neurochemical Research, 1986Identification of [14C]pipecolic acid (PA) receptors was attempted in the solubilized membrane fraction from rat cerebral cortex. Specific binding proteins for both PA and muscimol, a potent gamma-aminobutyric acid (GABA) agonist, were detected in the same preparation.
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Metabolism and uptake of -pipecolic acid by brain and heart
Life Sciences, 1981Abstract Metabolism and uptake of L -[1- 14 C]pipecolate was studied in the rat through tail vein injection at low (30 μg/kg) and high (30 mg/kg) doses. No radioactive compound other than L -pipecolate was detected in the brain or heart samples 0.5 to 60 min after injection. The contents of L -pipecolate in the brain dropped rapidly to
A K, Charles, Y F, Chang
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A short enantioselective synthesis of pipecolic acid
Tetrahedron: Asymmetry, 1995Abstract A simple enantioselective route to pipecolic acid is described. The key step involves the Sharpless asymmetric epoxidation of an N-protected aminoheptenol which spontaneously cyclises to a piperidine derivative on deprotection.
Concepción Fernández-García +1 more
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Asymmetric synthesis of pipecolic acid derivatives
Tetrahedron, 1992Abstract Condensation of chiral N-homoallyl β-amino alcohols with glyoxal produces iminium ions which are cyclized with complete stereoselectivity. These substrates, whose reactivity is closely dependent on the substitution pattern of the ethylenic moiety, undergo ene-iminium cyclizations that ultimately lead to homochiral pipecolic acid derivatives.
Claude Agami +3 more
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ChemInform, 1998
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
B. HO, T. M. ZABRISKIE
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AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
B. HO, T. M. ZABRISKIE
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Stereoselective synthesis of substituted pipecolic acids
Tetrahedron Letters, 1989Abstract The stereoselective synthesis of Δ 4,5 -pipecolic acid derivatives is described. The key step in the sequence is a [3,3] sigmatropic rearrangement.
Steven R. Angle, Damian O. Arnaiz
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New synthesis of pipecolic acid and analogs
Tetrahedron Letters, 1981Abstract Pipecolic acid congeners are synthesised from α-cyanoamides, obtained by substitution of α-methoxyamides with trimethylsilyl cyanide in an alternative route via oxidation of amidoalkylationproducts of the α-methoxyamides.
Vikram Asher +3 more
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