Total synthesis of luzopeptin E2

Angewandte Chemie - International Edition

Volumn 39, Issue 14, 2000, Pages 2493-2495

  Ciufolini, Marco A ^a   Valognes, Delphine ^a   Xi, Ning ^b  

^a Ecl Sup Chim Phys Electron L   (France)

^b RICE UNIVERSITY   (United States)

Author keywords

Antitumor agents; Depsipeptides; Macrocycles; Natural products; Total synthesis

Indexed keywords

LUZOPEPTIN;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS; REDUCTION;

EID: 0034679489     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2493::AID-ANIE2493>3.0.CO;2-5     Document Type: Article

References (29)

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13. D. L. Boger, M. W. Lederboer, M. Kume, M. Searcey, Q. Jin, J. Am. Chem. Soc. 1999, 121, 11375, Boger's landmark achievement followed an earlier disclosure of the synthesis of sandramycin, a congener of the peptins that contains pipecolinic acid and valine in place of piperazic acid and N-methyl-3-hydroxyvaline: D. L. Boger, J. H. Chen, K. W. Saionz, J. Am. Chem. Soc. 1996, 118, 1629. The Scripps team has also explored in further detail the bioactivity of peptins and related substances: D. L. Boger, J. H. Chen, K. W. Saionz, Q. Jin, Bioorg. Med. Chem. 1998, 6, 85; D. L. Boger, K. W. Saionz, Bioorg. Med. Chem. 1999, 7, 315.
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20. Molecular mechanics calculations suggested that the strain energy present in the peptin macrocycle per monomeric unit is less than half of the strain energy present in the cyclic form of each monomeric segment. If the transition state for acylative cyclization reactions were sufficiently late along the reaction coordinate, it seemed plausible that the relative energy content of products might influence product distribution. Details will be provided in forthcoming full papers.
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25. 4], the dimethallyl group resisted cleavage.
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