4.8 Article

Total synthesis of desferrisalmycin B

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 124, Issue 50, Pages 15001-15005

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja028386w

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Funding

  1. NIAID NIH HHS [AI 30988] Funding Source: Medline

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The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

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