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Lah, Myoung Soo
Nanoporous Materials Lab
Research Interests
  • Metal-Organic Frameworks (MOFs)

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Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations

Cited 29 times inthomson ciCited 30 times inthomson ci
Title
Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations
Author
Kang, EJCho, EJJi, MKLee, YEShin, DMChoi, SYChung, YKKim, JSKim, HJLee, SGLah, Myoung SooLee, E
Keywords
CHIRAL SYNTHESIS; NUCLEUS; ORGANOBORANES; DERIVATIVES; CALMODULIN; METABOLITE; COMPLEXES; ALDEHYDES; CHANNEL; REAGENT
Issue Date
200508
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.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.
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DOI
http://dx.doi.org/10.1021/jo0507993
ISSN
0022-3263
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