Highly Enantioselective Synthesis of (2S)‐α‐(Hydroxymethyl)‐glutamic Acid by the Catalytic Michael Addition of 2‐Naphthalen‐1‐yl‐2‐oxazoline‐4‐carboxylic Acid tert‐Butyl Ester.

Lee, Yeon‐Ju; Lee, Jihye; Kim, Mi‐Jeong; Jeong, Byeong‐Seon; Lee, Jeong‐Hee; Kim, Taek‐Soo; Lee, Jihoon; Ku, Jin‐Mo; Jew, Sang‐sup; Park, Hyeung‐geun

doi:10.1002/chin.200548192

Cited by 2 publications

(2 citation statements)

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“…The latter turned out to be the most challenging part of the synthesis. Related, albeit less complex amino acids, like lanthionine or diaminoglutamic acid either contain only four functional groups instead of five, as in the present case of labionin, or are not protected orthogonally8, 12, 13. Additionally the high density of functionalities easily leads to mostly undesired and disturbing intramolecular ring closing reactions14–16.…”

Section: Resultsmentioning

confidence: 95%

Synthetic studies toward labionin, a new α,α‐disubstituted amino acid from type III lantibiotic labyrinthopeptin A2

Sambeth

Süssmuth

2011

Journal of Peptide Science

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The labyrinthopeptins are a new class of lantibiotics containing two identical quaternary α,α-disubstituted amino acids, named labionin (Lab). The synthetic formation of this unique structural feature represents the key step in the total synthesis of these polycyclic peptides. In this report we describe the synthesis of an orthogonally protected α,α-disubstituted amino acid building block serving as labionin precursor for the future assembly of labyrinthopeptin A2 and of other labyrinthopeptin derivatives.

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Section: Resultsmentioning

confidence: 95%

Synthetic studies toward labionin, a new α,α‐disubstituted amino acid from type III lantibiotic labyrinthopeptin A2

Sambeth

Süssmuth

2011

Journal of Peptide Science

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“…80 Up to 97% ee could be obtained for the generation of glutamic acid analog 196, an excitatory neurotransmitter.…”

Section: Synthesis Of 175mentioning

confidence: 99%

Organocatalytic Conjugate Addition in Stereoselective Synthesis

Quintard

Alexakis

2013

Stereoselective Synthesis of Drugs and Natural Products

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Conjugate addition is a privileged method in organic synthesis allowing for the formation of new CC bonds, molecules that can serve as valuable synthons for total synthesis. It is highly attractive thanks to the presence of at least one functional group on the Michael partners, a group that can be easily derivatized. In this field, organocatalyzed reactions have recently changed the way of thinking about synthetic approaches, notably, as soon as carbonyl groups are involved. As a result, numerous applications of organocatalytic Michael additions in natural product synthesis have emerged in the last few years.

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Highly Enantioselective Synthesis of (2S)‐α‐(Hydroxymethyl)‐glutamic Acid by the Catalytic Michael Addition of 2‐Naphthalen‐1‐yl‐2‐oxazoline‐4‐carboxylic Acid tert‐Butyl Ester.

Cited by 2 publications

References 1 publication

Synthetic studies toward labionin, a new α,α‐disubstituted amino acid from type III lantibiotic labyrinthopeptin A2

Synthetic studies toward labionin, a new α,α‐disubstituted amino acid from type III lantibiotic labyrinthopeptin A2

Organocatalytic Conjugate Addition in Stereoselective Synthesis

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