Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

Szakonyi, Zsolt; Fülöp, Ferenc

doi:10.3998/ark.5550190.0004.e21

Cited by 3 publications

(2 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a convenient chiral natural source, (+)-myrtenal ( 160 ) was also efficiently used for the synthesis of cyclic β-amino acid enantiomers. Michael lithium amide trans-selective addition (for conjugate amine addition, see section ) to ester 161 ( derived from 160 ) gave 162 , the debenzylation and ester hydrolysis of which led to a novel monoterpene-based trans- β-amino acid ( 163 ) in enantiomerically pure form (Scheme ) …”

Section: Carbocyclic β-Amino Acidsmentioning

confidence: 99%

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

Self Cite

View full text Add to dashboard Cite

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

show abstract

Section: Carbocyclic β-Amino Acidsmentioning

confidence: 99%

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

Self Cite

View full text Add to dashboard Cite

show abstract

“…Various enantioselective methods are known for the synthesis of β-lactams. − Enantioselective methods or kinetic resolutions lead to enantiomeric β-lactams . Since nucleophilic attack opens the ring without difficulty, these compounds can be used as β-amino acid precursors. , When an amine is used as nucleophile, the product is the corresponding amide . The strategy is generally referred to as the β-lactam synthon method .…”

mentioning

confidence: 99%

A New Strategy To Produce β-Peptides: Use of Alicyclic β-Lactams

2004

Self Cite

View full text Add to dashboard Cite

show abstract

Stereoselective Synthesis and Cytoselective Toxicity of Monoterpene-Fused 2-Imino-1,3-thiazines

et al. 2014

Self Cite

View full text Add to dashboard Cite

Abstract:Starting from pinane-, apopinane-and carane-based 1,3-amino alcohols obtained from monoterpene-based β-amino acids, a library of monoterpene-fused 2-imino-1,3-thiazines as main products and 2-thioxo-1,3-oxazines as side-products were prepared via two-or three-step syntheses. When thiourea adducts prepared from 1,3-amino alcohols and aryl isothiocyanates were reacted with CDI under mild conditions, O-imidazolylcarbonyl intermediates were isolated which could be transformed to the desired 1,3-thiazines under microwave conditions. 1,3-Thiazines and 2-thioxo-1,3-oxazine side-products could also be prepared in one-step reactions through the application of CDI and microwave irradiation. The ring-closure process was extended to cycloalkane-based γ-hydroxythioureas. The carane-and apopinane-based derivatives exhibited marked antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, A2780, MCF7 and A431).

show abstract

Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

Cited by 3 publications

References 23 publications

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

A New Strategy To Produce β-Peptides: Use of Alicyclic β-Lactams

Stereoselective Synthesis and Cytoselective Toxicity of Monoterpene-Fused 2-Imino-1,3-thiazines

Contact Info

Product

Resources

About