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Synfacts 2007(5): 0457-0457
DOI: 10.1055/s-2007-968392
DOI: 10.1055/s-2007-968392
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Antibiotic GE2270A
Contributor(s):Philip KocienskiK. C. Nicolaou*, B. Zou, D. H. Dethe, D. B. Li, D. Y.-K. Chen
Agency for Science, Technology, and Research, Singapore; The Scripps Research Institute and University of California, San Diego, La Jolla, USA
Total Synthesis of Antibiotics GE2270A and GE2270T
Angew. Chem. Int. Ed. 2006, 45: 7786-7792
Agency for Science, Technology, and Research, Singapore; The Scripps Research Institute and University of California, San Diego, La Jolla, USA
Total Synthesis of Antibiotics GE2270A and GE2270T
Angew. Chem. Int. Ed. 2006, 45: 7786-7792
Further Information
Publication History
Publication Date:
24 April 2007 (online)
Key words
Diels-Alder reaction - pyridines -
Significance
G2270A is a thiopeptide antibiotic isolated from Planobispora rosea that inhibits bacterial elongation factor Tu but not the eukaryote elongation factor-1 alpha. The key step entails a hetero-Diels-Alder dimerization to generate the pyridine scaffold (red).
Comment
The hetero-Diels-Alder reaction used to construct the pyridine core was previously used in a synthesis of thiostreptone (K. C. Nicolaou et al. J. Am. Chem. Soc. 2005, 127, 11159-11175).