| Author | Cruz, Nilton Gonçalves da | |
| Author | Miranda, Amanda Silva de | |
| Author | Vieira, Henriete da Silva | |
| Author | Kohlhoff, Markus | |
| Author | Mendonça, João Guilherme Pereira | |
| Author | Diaz, Marisa Alves Nogueira | |
| Author | Diaz-Muñoz , Gaspar | |
| Access date | 2023-03-14T18:26:45Z | |
| Available date | 2023-03-14T18:26:45Z | |
| Document date | 2023 | |
| Citation | CRUZ, Nilton Gonçalves da et al. Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine. Synthesis, v. 55, A–I, p. 1-9, Jan. 2023. | en_US |
| ISSN | 0039-7881 | en_US |
| URI | https://www.arca.fiocruz.br/handle/icict/57370 | |
| Language | eng | en_US |
| Publisher | Thieme | en_US |
| Rights | restricted access | |
| Title | Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine | en_US |
| Type | Article | |
| DOI | 10.1055/a-1984-9689 | |
| Abstract | The enantioselective synthesis of the Hancock 1,2,3,4-tetrahydroquinoline alkaloids (S)-galipeine, (S)-cuspareine, (S)-galipinine, and (S)-angustureine and the nonnatural enantiomer (R)-galipeine is described herein. The target compounds were obtained in five steps from a racemic quinaldinic acid derived α-amino ester in overall yields of 21.2% to 37.5%. The synthetic route comprised two key steps: an enzymatic kinetic resolution to control the C-2 stereocenter, affording (R)- and (S)-α-amino esters as key chiral intermediates with 94% and 72% ee, respectively, and Wittig olefination of (R)- and (S)-α-amino aldehyde synthons with the corresponding phosphonium salts using a phase-transfer system (t-BuOH/CH2Cl2), thereby allowing the introduction of alkyl substituents at C-2. Finally, the enantioselective synthesis was concluded with the catalytic hydrogenation of olefinic bonds on the Wittig adducts to furnish the target Hancock alkaloids, including (R)-galipeine, whose synthesis is described here for the first time. | en_US |
| Affilliation | Department of Chemistry. Federal University of Minas Gerais. Belo Horizonte, MG, Brazil. | en_US |
| Affilliation | Department of Chemistry. Federal University of Minas Gerais. Belo Horizonte, MG, Brazil. | en_US |
| Affilliation | Department of Chemistry. Federal University of Minas Gerais. Belo Horizonte, MG, Brazil. | en_US |
| Affilliation | Oswaldo Cruz Foundation. René Rachou Institute. Chemistry of Bioactive Natural Products. Belo Horizonte, MG, Brazil. | en_US |
| Affilliation | Department of Biochemistry and Molecular Biology. Federal University of Viçosa. Viçosa, MG, Brazil. | en_US |
| Affilliation | Department of Biochemistry and Molecular Biology. Federal University of Viçosa. Viçosa, MG, Brazil. | en_US |
| Affilliation | Department of Chemistry. Federal University of Minas Gerais. Belo Horizonte, MG, Brazil. | en_US |
| Subject | Hancock alkaloids | en_US |
| Subject | Enzymatic kinetic resolution | en_US |
| Subject | Candida antarctica lipase | en_US |
| Subject | Wittig olefination | en_US |
| Embargo date | 2030-12-31 | |
