An Efficient Route to Either Enantiomer of<i>trans</i>-2-Aminocyclopentanecarboxylic Acid

LePlae, Paul R.; Umezawa, Naoki; Lee, Hee-Seung; Gellman, Samuel H.

doi:10.1021/jo010279h

Cited by 76 publications

(71 citation statements)

References 22 publications

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“…Several of them are depicted in Figure 2. Amipurimycin (5) and pitucamycin (6), containing five-and six-membered carbocyclic β-amino acid moieties, are antibiotics, while compounds 7−11 possess enzyme-inhibitory and antitumoral activities.…”

Section: 2a−dmentioning

confidence: 99%

“…Reduction of 29 with Na in i-PrOH led to transamino alcohol 30, which was converted by removal of the chiral auxiliary, N-Fmoc protection, and oxidation to trans-amino acid enantiomer 33. 6 An alternative simplified route has been described with the same chiral auxiliary. The enamine resulting from the reaction of keto ester 28 and (S)-α-methylbenzylamine was reduced with NaCNBH 3 to give trans-β-amino ester 31.…”

Section: I−smentioning

confidence: 99%

“…Ester hydrolysis, removal of the chiral auxiliary, and N-Fmoc protection led to amino acid 33 (Scheme 3). 6 Gellman et al applied this method to prepare enantiomerically pure 4,4-disubstituted derivatives of trans-β-aminocyclopentanecarboxylic acids. 7 The 4,4-disubstituted β-keto esters were reacted with (R)-α-methylbenzylamine and the resulting enamines were reduced with NaCNBH 3 .…”

Section: I−smentioning

confidence: 99%

“…1 The cyclic β-amino acids are not only pharmacologically active compounds themselves but are also elements in bioactive substances with more complex structures. Thus, amypurimycin (5) and pitucamycin (6), with five-and six-membered carbocyclic β-amino acid moieties, respectively, in their structure are antibiotics. 2g−k A large family of bioactive compounds is the nucleoside-based antibiotics, whose structures contain either five-or six-membered O-heterocyclic β-amino acid residues.…”

Section: Cyclic β-Amino Acids Possessing Antifungal or Antibacterial mentioning

confidence: 99%

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Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

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Introduction 1116 2. Carbocyclic β-Amino Acids 1118 2.1. Syntheses of Five-or Six-Membered Carbocyclic β-Amino Acids 1118 2.1.1. Carbocyclic β-Amino Acids from β-Keto Esters 1119 2.1.2. Carbocyclic β-Amino Acids by Metathesis 1119 2.1.3. Carbocyclic β-Amino Acids by Amino Group Conjugate Addition 1122 2.1.4. Carbocyclic β-Amino Acids by Cycloaddition 1124 2.1.5. Carbocyclic β-Amino Acids by Desymmetrization of meso-Anhydrides 1124 2.1.6. Carbocyclic β-Amino Acids from Natural Sources 1125 2.1.7. Miscellaneous 1127 2.2. Syntheses of Small-Ring Carbocyclic β-Amino Acids 1128 2.3. Syntheses of Carbocyclic β-Amino Acids with Larger Ring Systems 1129 2.4. Synthesis of Functionalized Carbocyclic β-Amino Acids 1131 2.4.1. Syntheses of Functionalized Cyclic β-Amino Acids by C−C Double Bond Functionalization 1131 2.4.2. Several Relevant Routes to Functionalized Cyclic β-Amino Acids Other Than Functionalization of the Ring C−C Double Bond 1137 3. Cyclic β-Amino Acids with a Heteroatom in the Ring 1137 3.1. Syntheses of Cyclic β-Amino Acids with a N Atom in the Ring 1138 3.1.1. Three-and Four-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.2. Five-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.3. Six-Membered N-Containing Cyclic β-Amino Acids 1145 3.1.4. N-Containing Cyclic β-Amino Acids with Larger Ring Systems 1148 3.2. Syntheses of Cyclic β-Amino Acids with an O Atom in the Ring 1148 3.2.1. Four-Membered O-Containing Cyclic β-Amino Acids 1148 3.2.2. Five-Membered O-Containing Cyclic β-Amino Acids 1149 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids 1155 3.3. Cyclic β-Amino Acids with Other Heteroatoms in the Ring 1159 4. Some Relevant Biological Properties of Cyclic β-Amino Acids 1160 4.1. Cyclic β-Amino Acids Possessing Antifungal or Antibacterial Properties 1160 4.2. Antiviral Cyclic β-Amino Acids 1162 4.3. Cyclic β-Amino Acids with Antitumoral Properties 1162 4.4. Cyclic β-Amino Acids with Cardioprotective

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Section: 2a−dmentioning

confidence: 99%

Section: I−smentioning

confidence: 99%

Section: I−smentioning

confidence: 99%

Section: Cyclic β-Amino Acids Possessing Antifungal or Antibacterial mentioning

confidence: 99%

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Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

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“…After the discovery of the H14 helix, systematic conformational searches and molecular dinamics calculations of the cyclopentane-containing trans-2-aminocyclopentanecarboxylic acid (trans-ACPC) revealed a new helical structure, the H12 helix [91][92][93][94][95][96][97][98] ( Figure 7). This helix type is stabilized by hydrogen-bonds between the residues at positions (i) and (i+3) in the sequence.…”

Section: Figure 4 Effects Of Substituents On the Torsional Angle θmentioning

confidence: 99%