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Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations
Cited 43 time in
Web of Science
Cited 48 time in Scopus
- Authors
- Issue Date
- 2005-08
- Publisher
- American Chemical Society
- Citation
- The Journal of Organic Chemistry, Vol.70 No.16, pp.6321-6329
- Abstract
- (+)-SCH 351448 (Na+ salt A) was synthesized employing ring-closing olefin metathesis reaction of an open diene diester intermediate for construction of the 28-membered macrodiolide structure. The open diene diester was prepared from the monomeric hydroxy carboxylic acid and two different olefin fragments. The monomeric hydroxy acid was synthesized via Julia-Julia coupling reaction of intermediates derived from the same olefinic fragments. Oxane units in these fragments were prepared by radical cyclization reactions of beta-alkoxyacrylates. Analogous SCH 351448 salts incorporating other mono- and divalent cations may be prepared. Under acidic conditions, SCH 351448 (Na+ salt A) was the most stable complex, but SCH 351448 (Ca2+ salt) and (Na+ salt B) appear to be physiologically important species.
- ISSN
- 0022-3263
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