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Synthesis of Orthogonally Protected Labionin.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2021 Mar 05; Vol. 86 (5), pp. 4313-4319. Date of Electronic Publication: 2021 Feb 18. - Publication Year :
- 2021
-
Abstract
- We report the first synthesis of the complex amino acid labionin in a fully orthogonally protected and stereopure form. The structure-which incorporates five orthogonal protecting groups and three stereogenic centers-was assembled using two key synthetic steps: (1) a thia-Michael addition for installing the thioether bridge; (2) an electrophilic azidation for creating the central quaternary α-amino acid carbon in a stereochemically pure form. This work is expected to enable the solid phase synthesis of both natural and synthetic analogues labyrinthopeptins.
- Subjects :
- Sulfides
Amino Acids
Solid-Phase Synthesis Techniques
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 86
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 33599506
- Full Text :
- https://doi.org/10.1021/acs.joc.0c02922