title: Stereoselective synthesis of (+)-SCH 351448: a unique ligand system for sodium, calcium, and other cations.
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.
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea.
authors.forename: Eun Joo
authors.initials: EJ
authors.lastname: Kang
authors.forename: Eun Jin
authors.initials: EJ
authors.lastname: Cho
authors.forename: Mi Kyung
authors.initials: MK
authors.lastname: Ji
authors.forename: Young Eun
authors.initials: YE
authors.lastname: Lee
authors.forename: Dong Mok
authors.initials: DM
authors.lastname: Shin
authors.forename: Soo Young
authors.initials: SY
authors.lastname: Choi
authors.forename: Young Keun
authors.initials: YK
authors.lastname: Chung
authors.forename: Jong-Seo
authors.initials: JS
authors.lastname: Kim
authors.forename: Hie-Joon
authors.initials: HJ
authors.lastname: Kim
authors.forename: Sueg-Geun
authors.initials: SG
authors.lastname: Lee
authors.forename: Myoung Soo
authors.initials: MS
authors.lastname: Lah
authors.forename: Eun
authors.initials: E
authors.lastname: Lee
mesh_terms: D002118:Calcium / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D012964:Sodium / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D002412:Cations; D007783:Lactones; D008024:Ligands; C451479:SCH 351448; D012997:Solvents; D012964:Sodium; D002118:Calcium