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Total Synthesis of Dynobactin A.
Schneider, Fabian; Guo, Yinliang; Lin, You-Chen; Eberle, Kelly J; Chiodi, Debora; Greene, Johnathan A; Lu, Chenxin; Baran, Phil S.
Affiliation
  • Schneider F; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Guo Y; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Lin YC; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Eberle KJ; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Chiodi D; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Greene JA; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Lu C; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  • Baran PS; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
J Am Chem Soc ; 146(10): 6444-6448, 2024 03 13.
Article in En | MEDLINE | ID: mdl-38427590
ABSTRACT
The first total synthesis of the potent antimicrobial agent dynobactin A is disclosed. This synthesis enlists a singular aziridine ring opening strategy to access the two disparate ß-aryl-branched amino acids present within this complex decapeptide. Featuring a number of unique maneuvers to navigate inherently sensitive and epimerizable functional groups, this convergent approach proceeds in only 16 steps (LLS) from commercial materials and should facilitate the synthesis of numerous analogues for medicinal chemistry studies.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Amino Acids / Anti-Infective Agents Language: En Journal: J Am Chem Soc / Journal of the american chemical society / J. am. chem. soc Year: 2024 Document type: Article Affiliation country: United States Country of publication: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Amino Acids / Anti-Infective Agents Language: En Journal: J Am Chem Soc / Journal of the american chemical society / J. am. chem. soc Year: 2024 Document type: Article Affiliation country: United States Country of publication: United States