Related Experiment Video
Updated: Mar 28, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Stereocontrolled synthesis of rosuvastatin calcium via iodine chloride-induced intramolecular cyclization
Fangjun Xiong1, Haifeng Wang, Lingjie Yan
1Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, People's Republic of China. rfchen@fudan.edu.cn wywin8@163.com.
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.
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Esters to β-Ketoesters: Claisen Condensation Mechanism
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
SN1 Reaction: Stereochemistry
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
