Highly Stereoselective Formal Synthesis of Rosuvastatin and Pitavastatin Through Julia–Kocienski Olefination Using the Lactonized Statin Side-Chain Precursor

Autor:	Jan Fabris, Zdenko Časar, Ivana Gazic Smilovic, Martin Črnugelj
Rok vydání:	2014
Předmět:	Pyrimidine Chemistry Stereochemistry Organic Chemistry Quinoline Catalysis Sulfone chemistry.chemical_compound medicine Side chain Stereoselectivity Rosuvastatin Pitavastatin Derivative (chemistry) medicine.drug
Zdroj:	Synthesis. 46:2333-2346
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0033-1338648
Popis:	An expedient and simple synthetic approach to pitava­statin and rosuvastatin final intermediates is described. The presented approach consists of completely stereoselective Julia–Kocienski olefination step (E/Z up to 300:1) between lactonized statin side-chain precursor and sulfone derivative of the corresponding pyrimidine and quinoline heterocyclic cores. The desired O-TBS protected statin lactones were isolated in 66–71% yield and high >97% purity (HPLC).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fc733986048112939c1e55f15fe11338 https://doi.org/10.1055/s-0033-1338648 Zobrazit plný text záznamu