Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper ReagentsSynthesis of (-)-Lardolure and Siphonarienal

Morozova, Varvara; Skotnitzki, Juri; Moriya, Kohei; Karaghiosoff, Konstantin und Knochel, Paul (2018): Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper ReagentsSynthesis of (-)-Lardolure and Siphonarienal. In: Angewandte Chemie-International Edition, Bd. 57, Nr. 19: S. 5516-5519

Abstract

Optically enriched secondary alkyl iodides were converted into secondary alkyllithium and secondary alkylcopper compounds with very high retention of configuration. Quenching with various electrophiles, including chiral epoxides, provided a range of chiral molecules with high enantiomeric purity (>90%ee). This method has been applied in an iterative fashion in the total synthesis of (-)-lardolure in 13 steps and 5.4% overall yield (>99%ee, dr>99:1) and siphonarienal in 15 steps and 5.6% overall yield (>99%ee, dr>99:1) starting from commercially available ethyl (R)-3-hydroxybutyrate (>99%ee).

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1433-7851
• Sprache: Englisch