Concise and scalable synthesis of (±)-phosphonothrixin

• Published in: Results in Chemistry Vol. 3; p. 100251
• Main Authors: Matsushima, Yoshitaka, Nakamura, Koki
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.01.2021; Elsevier
• Subjects: (±)-Phosphonothrixin; C–P bond; Herbicidal antibiotic; Scalable synthesis; Herbicidal antibiotic; C–P bond; Scalable synthesis; (±)-Phosphonothrixin
• ISSN: 2211-7156; 2211-7156
• DOI: 10.1016/j.rechem.2021.100251

[Display omitted] •A concise and scalable method for the synthesis of (±)-phosphonothrixin (total 18% yield in 6 steps).•Phosphonothrixin is an herbicidal antibiotic containing a C–P bond.•A simpler and more responsible method for the synthetic precursor was developed. A concise and scalable method for the synthesis of (±)-phosphonothrixin (1), an herbicidal antibiotic containing a C–P bond, was developed. We developed a simpler and more responsible method for the synthetic precursor, epoxy alcohol 2. The synthetic route is efficient, requiring only six steps to isolate (±)-1 (18%) from the easily obtainable known epoxy alcohol 3 and can be applied to enable gram-scale synthesis.