Biomimetic synthesis of Cbz-(S)-dolaphenine

Biomimetic synthesis of Cbz-(S)-dolaphenine

A new route to Cbz-(S)-dolaphenine, a recurring element in bioactive peptidic natural products, has been implemented, which closely parallels the biogenetic pathway. Cyclodehydration of 11 to yield thiazoline 2 allows for a Ni(0)-promoted decarbonylative aromatization to provide the thiazole framewo...

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Veröffentlicht in:Tetrahedron letters 2012-09, Vol.53 (37), p.4989-4993
Hauptverfasser: García-Reynaga, Pablo, VanNieuwenhze, Michael S.
Format: Artikel
Sprache:eng
Schlagworte:
bioactive properties
Biocompatibility
Biomimetic
biomimetic synthesis
Biomimetics
chemical reactions
chemical structure
Cyclodehydration
Decarbonylation
Natural products
nickel
organic compounds
Pathways
Stereochemistry
Synthesis (chemistry)
Tetrahedrons
Thiazole
Thiazoline
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Beschreibung
Zusammenfassung:A new route to Cbz-(S)-dolaphenine, a recurring element in bioactive peptidic natural products, has been implemented, which closely parallels the biogenetic pathway. Cyclodehydration of 11 to yield thiazoline 2 allows for a Ni(0)-promoted decarbonylative aromatization to provide the thiazole framework with retention of stereochemistry.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.07.027