A Comparative Synthetic Strategy Perspective on α‐Amino Acid‐ and Non‐Amino Acid‐Derived Synthons towards Total Syntheses of Selected Natural Macrolides

Manda, Srinivas Lavanya Kumar; Tripathi, Shashank; Ghoshal, Anirban; Ambule, Mayur D.; Srivastava, Ajay Kumar; Panda, Gautam

doi:10.1002/chem.201904564

Cited by 12 publications

(2 citation statements)

References 140 publications

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“…Chiral natural and unnatural amino acids are privileged compounds in the preparation of chiral medicines, bioactive peptides, chiral auxiliaries, catalysts, and synthetic intermediates . Thousands of publications have demonstrated synthetic methods due to the importance of these products .…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Reduction of Aromatic α-Dehydroamino Acid Esters with Water as Hydrogen Source

et al. 2021

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The asymmetric reduction of aromatic α-dehydroamino acid esters with water as the hydrogen source was developed by a Rh/Cu co-catalytic system. The reaction tolerates various functional groups, providing a valuable synthetic tool to access chiral α-amino acid esters readily. Moreover, the present methodology also was applied in the cost-effective and easy to handle preparation of chiral deuterated α-amino esters by using D2O.

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Section: Introductionmentioning

confidence: 99%

Asymmetric Reduction of Aromatic α-Dehydroamino Acid Esters with Water as Hydrogen Source

et al. 2021

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“…3 The construction of α-AAs with vicinal stereocenters is difficult owing to the steric hindrance. 4,5 Particularly, the synthesis of α-AAs bearing vicinal tetrasubstituted stereocenters is the most challenging in asymmetric catalysis and only limited examples have been reported. 6 Oxindole represents a class of valuable scaffold in medicinal chemistry, and a wide array of transformations based on oxindoles has been established.…”

Section: ■ Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Oxindole-Derived Vicinal Tetrasubstituted Acyclic Amino Acid Derivatives by the Mannich-Type Reaction

et al. 2020

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The catalytic asymmetric Mannich-type reaction of 3-hydroxy/3-aminooxindoles with 2-aminoacrylates to afford oxindole-derived acyclic amino acid derivatives bearing vicinal tetrasubstituted stereocenters is reported. (DHQ)2PHAL (4g) and quinine-derived squaramide (4d) were identified as efficient catalysts. Transformations of the Mannich-type reaction products highlight the utility of this synthetic strategy.

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Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

et al. 2022

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A selective ring‐closing metathesis (RCM) reaction for the formation of large macrocycles by using latent sulfur chelated ruthenium iodide benzylidenes, readily activated by thermal and photochemical (UV‐A and visible light) stimuli, is reported. For dienes having one terminal alkene and one internal double bond, the specific affinity of diiodo ruthenium alkylidenes for the unhindered terminus, combined with their reluctance to react with internal olefins, favors RCM over oligomerization, providing high macrocyclic yields even at relatively high concentrations. Alternatively, for substrates containing two internal double bonds, a sacrificial methylene donor can be used to obtain the desired products. With this methodology, lactones, lactams, and macrocyclic ketones ranging from 13‐ to 22‐membered rings could be synthesized in moderate to high yields. In addition, synthetic applications for a one‐pot cyclization/reduction sequence to produce Exaltolide, a natural macrolide (commercial musk), Dihydrocivetone, and other saturated macrocycles have been explored. Thus, we disclose herein an important advantage for diiodo ruthenium benzylidene catalysts over their less selective dichloro counterparts and provide a more profound understanding of the mechanisms that provide the enhanced cyclization outcome.

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A Comparative Synthetic Strategy Perspective on α‐Amino Acid‐ and Non‐Amino Acid‐Derived Synthons towards Total Syntheses of Selected Natural Macrolides

Cited by 12 publications

References 140 publications

Asymmetric Reduction of Aromatic α-Dehydroamino Acid Esters with Water as Hydrogen Source

Asymmetric Reduction of Aromatic α-Dehydroamino Acid Esters with Water as Hydrogen Source

Asymmetric Synthesis of Oxindole-Derived Vicinal Tetrasubstituted Acyclic Amino Acid Derivatives by the Mannich-Type Reaction

Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

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