856242-91-6Relevant academic research and scientific papers
Enantioselective Total Synthesis of Erogorgiaene: Applications of Asymmetric Cu-Catalyzed Conjugate Additions of Alkylzincs to Acyclic Enones
Cesati III, Richard R.,De Armas, Judith,Hoveyda, Amir H.
, p. 96 - 101 (2007/10/03)
The first enantioselective synthesis of erogorgiaene (1), an inhibitor of mycobacterium tuberculosis, is disclosed. The total synthesis highlights the utility of asymmetric conjugate additions (ACA) of alkylzincs to acyclic α,β-unsaturated ketones catalyzed by peptidic phosphine ligands and (CuOTf)2·C6H6. Moreover, several critical attributes of this catalytic C-C bond-forming reaction are illustrated in the context of the total synthesis; these include the significance of various structural features of the amino acid-based chiral ligands and the chiral ligand's effectiveness in reactions involving achiral and chiral substrates. In addition, the total synthesis showcases some of the special properties of nonphosphine Ru complex 3 as a highly effective catalyst for olefin cross-metathesis.
