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Biomimetic Synthesis of Cbz-(S)-Dolaphenine.

ABSTRACT: 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.

SUBMITTER: Garcia-Reynaga P

PROVIDER: S-EPMC3488445 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Biomimetic Synthesis of Cbz-(S)-Dolaphenine.

García-Reynaga Pablo P Vannieuwenhze Michael S MS

Tetrahedron letters 20120901 37

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. ...[more]

PMID: 23136451

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