Enantioselective synthesis of (+)-gossonorol and related systems using organozinc reagents

Autor:	Susana González-López, Miguel Yus, Diego J. Ramón
Rok vydání:	2012
Předmět:	Natural product Chemistry Ligand Organic Chemistry Dimethylzinc Enantioselective synthesis Catalysis Inorganic Chemistry chemistry.chemical_compound Nucleophile Reagent Yield (chemistry) Organic chemistry Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry. 23:611-615
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2012.04.003
Popis:	The sesquiterpene (+)-gossonorol is prepared in only three synthetic steps in 60% overall yield and 82% ee from commercially available reagents. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to 5-methyl-1-(2-methylphenyl)hex-4-en-1-one catalyzed by chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The modular approach allows the synthesis not only of the aforementioned natural product but also other products arising from the corresponding processes of ethylation, phenylation, and ethynylation, just by changing the final nucleophilic reagent and using the same isoborneol type ligand.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f959862ff2f7d9fd632fbe3a7609a43b https://doi.org/10.1016/j.tetasy.2012.04.003 Zobrazit plný text záznamu Full Text from ScienceDirect