Tetrahedron: Asymmetry

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

S González-López, M Yus, DJ Ramón

Index: Gonzalez-Lopez, Susana; Yus, Miguel; Ramon, Diego J. Tetrahedron Asymmetry, 2012 , vol. 23, # 8 p. 611 - 615

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Citation Number: 8

Abstract

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 ...