Total Synthesis of Salinosporamide A

Total Synthesis of Salinosporamide A

Total synthesis of potent proteasome inhibitor salinosporamide A (1) has been accomplished, which features strictly substrate-controlled operations starting with the only chiral center of (R)-pyroglutamic acid. The consecutive quaternary carbons within 1 have been efficiently constructed by manipula...

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Veröffentlicht in:Journal of the American Chemical Society 2005-06, Vol.127 (23), p.8298-8299
Hauptverfasser: Endo, Atsushi, Danishefsky, Samuel J
Format: Artikel
Sprache:eng
Schlagworte:
Actinomycetales - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Lactones - chemical synthesis
Organic chemistry
Preparations and properties
Protease Inhibitors - chemical synthesis
Pyrroles - chemical synthesis
Selenium - chemistry
Stereoisomerism
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Zusammenfassung:Total synthesis of potent proteasome inhibitor salinosporamide A (1) has been accomplished, which features strictly substrate-controlled operations starting with the only chiral center of (R)-pyroglutamic acid. The consecutive quaternary carbons within 1 have been efficiently constructed by manipulation of two intramolecular reactions:  (1) carbonate-mediated internal acylation of imidate ester (4 → 14) and (2) selenocyclization of aldehyde to exocyclic methylene group (5 → 18).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0522783