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Advanced Search

  • Type of publication
    • Publication 26
  • Year
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  • Journal / Volume / Preprint Server Sorted by frequency and by alphabetical order
    • Phytochemistry 366
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  • Author Sorted by frequency and by alphabetical order
    • Wessjohann, L. 18
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      de Meijere, A. 3
      Neves Filho, R. A. W. 2
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Publications

Puentes, A. R.; Neves Filho, R. A. W.; Rivera, D. G.; Wessjohann, L. A.; Total Synthesis of Cordyheptapeptide A Synlett 28 1971-1974 (2017) DOI: 10.1055/s-0036-1588433
  • Abstract
  • BibText
  • RIS

The first total synthesis of cordyheptapeptide A is described. The synthesis is accomplished by a convergent approach featuring a combination of peptide coupling and the Ugi reaction for the preparation of the main building blocks and the acyclic precursor. The assembly of an N-methylated fragment by the Ugi reaction comprised the utilization of a convertible isonitrile followed by activation of the C-terminal amide. Two different macrocyclization sites were evaluated, proving greater efficacy the macrolactamization at the site Ile-Tyr, likely due of a more suitable conformational bias of the acyclic precursor having an internal β-turn centered at the N-Me-d-Phe-Pro moiety.

Publications

Puentes, A. R.; Neves Filho, R. A. W.; Rivera, D. G.; Wessjohann, L. A.; Total Synthesis of Cordyheptapeptide A Synlett 28 1971-1974 (2017) DOI: 10.1055/s-0036-1588433
  • Abstract
  • BibText
  • RIS

The first total synthesis of cordyheptapeptide A is described. The synthesis is accomplished by a convergent approach featuring a combination of peptide coupling and the Ugi reaction for the preparation of the main building blocks and the acyclic precursor. The assembly of an N-methylated fragment by the Ugi reaction comprised the utilization of a convertible isonitrile followed by activation of the C-terminal amide. Two different macrocyclization sites were evaluated, proving greater efficacy the macrolactamization at the site Ile-Tyr, likely due of a more suitable conformational bias of the acyclic precursor having an internal β-turn centered at the N-Me-d-Phe-Pro moiety.

Publications

Ayaz, M.; Westermann, B.; Enantioenriched Naphthoquinone Mannich Bases by Organocatalyzed Nucleophilic Additions to in situ Formed Imines Synlett 2010 1489-1492 (2010) DOI: 10.1055/s-0029-1219946
  • Abstract
  • BibText
  • RIS

Organocatalytic nucleophilic addition of 2-hydroxylnaphthaquinone to imines is reported. This new route can be used to produce enantioenriched Mannich bases with excellent yields and moderate enantioselectivities.

Publications

Ayaz, M.; Westermann, B.; Enantioenriched Naphthoquinone Mannich Bases by Organocatalyzed Nucleophilic Additions to in situ Formed Imines Synlett 2010 1489-1492 (2010) DOI: 10.1055/s-0029-1219946
  • Abstract
  • BibText
  • RIS

Organocatalytic nucleophilic addition of 2-hydroxylnaphthaquinone to imines is reported. This new route can be used to produce enantioenriched Mannich bases with excellent yields and moderate enantioselectivities.

Publications

Ayaz, M.; Westermann, B.; Enantioenriched Naphthoquinone Mannich Bases by Organocatalyzed Nucleophilic Additions to in situ Formed Imines Synlett 2010 1489-1492 (2010) DOI: 10.1055/s-0029-1219946
  • Abstract
  • BibText
  • RIS

Organocatalytic nucleophilic addition of 2-hydroxylnaphthaquinone to imines is reported. This new route can be used to produce enantioenriched Mannich bases with excellent yields and moderate enantioselectivities.

Publications

Rivera, D.; Vercillo, O.; Wessjohann, L.; Combinatorial Synthesis of Macrocycles by Multiple Multicomponent Macrocyclization Including Bifunctional Building Blocks (MiB) Synlett 2007 0308-0312 (2007) DOI: 10.1055/s-2007-968006
  • Abstract
  • BibText
  • RIS

Small libraries of peptoid-based macro(multi)cycles were produced by applying combinatorial principles to the MiB methodology. This combinatorial approach features the incorporation of varied building blocks into the resulting macrocycles by mixing all the components in the same reaction pot. Both skeletal and appendage diversity could be generated in one shot due to the multicomponent nature of the system. HPLC and ESI-MS analyses showed a well-distributed composition of the libraries and revealed the presence of all possible macrocycles resulting from the different combinations of building blocks, especially of members with differentially substituted bridges not available by any other one-pot ­approach.

Publications

Kreye, O.; Westermann, B.; Wessjohann, L.; A Stable, Convertible Isonitrile as a Formic Acid Carbanion [-COOH] Equivalent and Its Application in Multicomponent Reactions Synlett 2007 3188-3192 (2007) DOI: 10.1055/s-2007-990912
  • Abstract
  • BibText
  • RIS

The application of 2-(2,2-dimethoxyethyl) phenyl iso­nitrile in Ugi, Passerini, and Ugi-Smiles reactions is described. The simple transformation to highly activated indolyl amides allows functional-group conversion of the isonitrile moiety into a variety of carboxylic acid derivatives, overall acting as a neutral, nucleophilic COOH equivalent.

Publications

Braga, A.; Paixao, M.; Westermann, B.; Schneider, P.; Wessjohann, L.; Aziridine-Modified Amino Alcohols as Efficient Modular Catalysts for Highly Enantioselective Alkenylzinc Additions to Aldehydes Synlett 2007 0917-0920 (2007) DOI: 10.1055/s-2007-973879
  • Abstract
  • BibText
  • RIS

N-Tritylaziridino alcohols have been easily synthesized in a straightforward synthetic route from an inexpensive and easily available chiral pool. They were used in the enantioselective alkenylzinc additions to aldehydes furnishing the products in excellent yields and stereoselectivities up to 97%.

Publications

Wessjohann, L.; Schmidt, G.; Schrekker, H.; The Chromium(II)-Mediated Coupling of Secondary Alkylhalides with Aromatic Aldehydes Synlett 2007 2139-2141 (2007) DOI: 10.1055/s-2007-984887
  • Abstract
  • BibText
  • RIS

The scope of chromium(II)-mediated Takai-Utimoto ­reactions was extended to previously unconvertable secondary alkylhalides. Optimization allowed yields of up to over 95%.

Publications

Rivera, D.; Vercillo, O.; Wessjohann, L.; Combinatorial Synthesis of Macrocycles by Multiple Multicomponent Macrocyclization Including Bifunctional Building Blocks (MiB) Synlett 2007 0308-0312 (2007) DOI: 10.1055/s-2007-968006
  • Abstract
  • BibText
  • RIS

Small libraries of peptoid-based macro(multi)cycles were produced by applying combinatorial principles to the MiB methodology. This combinatorial approach features the incorporation of varied building blocks into the resulting macrocycles by mixing all the components in the same reaction pot. Both skeletal and appendage diversity could be generated in one shot due to the multicomponent nature of the system. HPLC and ESI-MS analyses showed a well-distributed composition of the libraries and revealed the presence of all possible macrocycles resulting from the different combinations of building blocks, especially of members with differentially substituted bridges not available by any other one-pot ­approach.

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