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

Morozova, Varvara; Skotnitzki, Juri; Moriya, Kohei; Karaghiosoff, Konstantin and Knochel, Paul (2018): Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper ReagentsSynthesis of (-)-Lardolure and Siphonarienal. In: Angewandte Chemie-International Edition, Vol. 57, No. 19: pp. 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).

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English