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Concise synthesis of capuramycin.

ABSTRACT: A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4'',5''-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with >30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.

SUBMITTER: Kurosu M

PROVIDER: S-EPMC4784474 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Concise synthesis of capuramycin.

Kurosu Michio M Li Kai K Crick Dean C DC

Organic letters 20090601 11

A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4'',5''-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with >30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin. ...[more]

PMID: 19405507

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