title: Concise diastereoselective synthesis of calcaripeptide C via asymmetric transfer hydrogenation/Pd-induced chiral allenylzinc as a key reaction.
abstract: Synthesis of the natural product calcaripeptide C derived from the fungal metabolite mycelium KF525 of Calcarisporium sp. has been achieved. This complementary approach avoids the use of a stoichiometric amount of chiral auxiliary reagents as commonly used to generate enantioenriched advanced precursors. The enantioselective synthesis of calcaripeptide C is remarkable in that using catalytic reactions sets the two stereogenic centers efficiently with good levels of enantioselectivity. Further diversification of the calcaripeptide C structures is possible by employing a complementary catalytic enantioenriched Ru-catalyst.
authors.affiliation: Organic & Biomolecular Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500 607, India. gkswamy_iict@yahoo.co.in.
authors.forename: Gullapalli
authors.initials: G
authors.lastname: Kumaraswamy
authors.forename: Vykunthapu
authors.initials: V
authors.lastname: Narayanarao
authors.forename: Ragam
authors.initials: R
authors.lastname: Raju
mesh_terms: D002384:Catalysis; D047630:Depsipeptides / Q000737:chemistry*; D006865:Hydrogenation; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D047630:Depsipeptides; D009942:Organometallic Compounds; C584593:calcaripeptide C; D010165:Palladium