title: Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereoselective synthesis of iridoid natural products.
abstract: [reaction: see text] Iridoid natural products 1-4 are accessed stereoselectively by means of tridentate (Schiff base)Cr(III)-catalyzed hetero-Diels-Alder reactions between ethyl vinyl ether and enantioenriched 5-methyl-1-cyclopentene-1-carboxaldehyde. An efficient route to the aldehyde from citronellal is afforded by the ring-closing metathesis reaction.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: David E
authors.initials: DE
authors.lastname: Chavez
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D004583:Electrons; D013237:Stereoisomerism
chemical_list: D001688:Biological Products