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Stereoselective Synthesis of (+)-SCH 351448:  A Unique Ligand System for Sodium, Calcium, and Other Cations

Title
Stereoselective Synthesis of (+)-SCH 351448:  A Unique Ligand System for Sodium, Calcium, and Other Cations
Author
나명수
Issue Date
2005-08
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v. 70, No. 16, Page. 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.
URI
https://pubs.acs.org/doi/abs/10.1021/jo0507993http://repository.hanyang.ac.kr/handle/20.500.11754/111383
ISSN
0022-3263; 1520-6904
DOI
10.1021/jo0507993
Appears in Collections:
COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > ETC
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