Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations
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- Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations
- Kang, EJ; Cho, EJ; Ji, MK; Lee, YE; Shin, DM; Choi, SY; Chung, YK; Kim, JS; Kim, HJ; Lee, SG; Lah, Myoung Soo; Lee, E
- CHIRAL SYNTHESIS; NUCLEUS; ORGANOBORANES; DERIVATIVES; CALMODULIN; METABOLITE; COMPLEXES; ALDEHYDES; CHANNEL; REAGENT
- Issue Date
- AMER CHEMICAL SOC
- JOURNAL OF ORGANIC CHEMISTRY, v.70, no.16, pp.6321 - 6329
- (+)-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.
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