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Isolation, Structure, and Total Synthesis of the Marine Macrolide Mangrolide D.

ABSTRACT: The isolation, characterization, and total synthesis of the macrocyclic polyene mangrolide D is reported. A 16-step total synthesis relies on robust Suzuki and ring-closing metathesis reactions, and an iron-catalyzed hydroazidation of an exomethylene substituted tetrahydropyran as a key step for the synthesis of the appended 4- epi-vancosamine sugar. Although mangrolide D did not display antibiotic activity, this work should prove enabling toward the synthesis of the antitubercular tiacumicins which display a virtually identical macrocyclic backbone.

SUBMITTER: Gong J

PROVIDER: S-EPMC6526702 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Isolation, Structure, and Total Synthesis of the Marine Macrolide Mangrolide D.

Gong Junyu J Li Wei W Fu Peng P MacMillan John J De Brabander Jef K JK

Organic letters 20190408 8

The isolation, characterization, and total synthesis of the macrocyclic polyene mangrolide D is reported. A 16-step total synthesis relies on robust Suzuki and ring-closing metathesis reactions, and an iron-catalyzed hydroazidation of an exomethylene substituted tetrahydropyran as a key step for the synthesis of the appended 4- epi-vancosamine sugar. Although mangrolide D did not display antibiotic activity, this work should prove enabling toward the synthesis of the antitubercular tiacumicins w ...[more]

PMID: 30957503

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