title: Stereocontrolled synthesis of rosuvastatin calcium via iodine chloride-induced intramolecular cyclization.
abstract: A novel, stereoselective approach towards rosuvastatin calcium from the known (S)-homoallylic alcohol has been developed. The synthesis is highlighted by a regio- and stereocontrolled ICl-induced intramolecular cyclization of chiral homoallylic carbonate to deliver the C6-formyl statin side chain with a syn-1,3-diol moiety. An improved synthesis of the rosuvastatin pyrimidine core moiety is also included. Moreover, this methodology is useful in the asymmetric synthesis of structural variants of statins such as pitavastatin calcium and atorvastatin calcium and their related analogs.
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, People's Republic of China. rfchen@fudan.edu.cn wywin8@163.com.
authors.forename: Fangjun
authors.initials: F
authors.lastname: Xiong
authors.forename: Haifeng
authors.initials: H
authors.lastname: Wang
authors.forename: Lingjie
authors.initials: L
authors.lastname: Yan
authors.forename: Sheng
authors.initials: S
authors.lastname: Han
authors.forename: Yuan
authors.initials: Y
authors.lastname: Tao
authors.forename: Yan
authors.initials: Y
authors.lastname: Wu
authors.forename: Fener
authors.initials: F
authors.lastname: Chen
mesh_terms: D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D000068718:Rosuvastatin Calcium / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002712:Chlorides; D000068718:Rosuvastatin Calcium; D007455:Iodine