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

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

Abstract 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 deriv...

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Veröffentlicht in:Synthesis (Stuttgart) 2014-09, Vol.46 (17), p.2333-2346
Hauptverfasser: Fabris, Jan, Časar, Zdenko, Smilović, Ivana Gazić, Črnugelj, Martin
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract 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).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1338648