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Total syntheses of linear polythiazole/oxazole plantazolicin A and its biosynthetic precursor plantazolicin B.

ABSTRACT: Plantazolicin?A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin?A and its biosynthetic precursor plantazolicin?B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4-concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin?B and includes the first complete characterization data for both natural products.

SUBMITTER: Wilson ZE

PROVIDER: S-EPMC4464531 | biostudies-other | 2015 Jan

REPOSITORIES: biostudies-other

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Total syntheses of linear polythiazole/oxazole plantazolicin A and its biosynthetic precursor plantazolicin B.

Wilson Zoe E ZE Fenner Sabine S Ley Steven V SV

Angewandte Chemie (International ed. in English) 20141125 4

Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4-concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin B and includ ...[more]

PMID: 25424526

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