Optimization synthesis of phosphorous-containing natural products fosmidomycin and FR900098

Abstract Fosmidomycin and its acetyl analogue FR900098 are two phosphorus-containing natural products with inhibitory activity against IspC enzyme in the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway of isoprenoid biosynthesis in plants and most bacteria. This work presents a facile route for the chemical synthesis of fosmidomycin and FR900098 using readily available raw materials. Through optimizing reaction conditions of the key steps of Michaelis-Becker reaction and acylation, the monosodium salts of fosmidomycin and FR900098 were obtained in yields of 60% and 66%, respectively, over six steps in the route. This unified route provides an alternative to the reported methods and makes it possible to synthesize the two valuable compounds with scalability and low cost, having the potential for application in developing new antimalarial drugs and pesticides. Graphical Abstract

• Publication year

  2023

• Venue

  Phosphorus Sulfur and Silicon and the Related Elements

• Publication date

  2023-02-02

• Fields of study

  Not labeled

• Identifiers
  DOI 10.1080/10426507.2023.2173756
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

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