title: Enantioselective total synthesis of erogorgiaene: applications of asymmetric Cu-catalyzed conjugate additions of alkylzincs to acyclic enones.
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 alpha,beta-unsaturated ketones catalyzed by peptidic phosphine ligands and (CuOTf)(2).C(6)H(6). 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.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Richard R
authors.initials: RR
authors.lastname: Cesati
authors.forename: Judith
authors.initials: J
authors.lastname: de Armas
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002074:Butanones; D004224:Diterpenes; D007659:Ketones; D009942:Organometallic Compounds; C428183:erogorgiaene; D003300:Copper; C057920:3-buten-2-one; D015032:Zinc