Enantioselective Total Synthesis of Erogorgiaene: Applications of Asymmetric Cu-Catalyzed Conjugate Additions of Alkylzincs to Acyclic Enones
- 13 December 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (1) , 96-101
- https://doi.org/10.1021/ja0305407
Abstract
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.Keywords
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