Stereoselective synthesis of (+)-SCH 351448: a unique ligand system for sodium, calcium, and other cations.
(+)-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.
Kang
Eun Joo
EJ
Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea.
Cho
Eun Jin
EJ
Ji
Mi Kyung
MK
Lee
Young Eun
YE
Shin
Dong Mok
DM
Choi
Soo Young
SY
Chung
Young Keun
YK
Kim
Jong-Seo
JS
Kim
Hie-Joon
HJ
Lee
Sueg-Geun
SG
Lah
Myoung Soo
MS
Lee
Eun
E
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
D002412:Cations; D007783:Lactones; D008024:Ligands; C451479:SCH 351448; D012997:Solvents; D012964:Sodium; D002118:Calcium