title: Diastereoselective synthesis of the endo- and exo-spirotetronate subunits of the quartromicins. The first enantioselective Diels-Alder reaction of an acyclic (Z)-1,3-diene.
abstract: [reaction: see text]. Diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of quartromicins A3 and D3, are described. The key step of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels-Alder reactions of the 1,1,3,4-tetrasubstituted diene 3.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA. roush@umich.edu
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
authors.forename: Chris
authors.initials: C
authors.lastname: Limberakis
authors.forename: Roxanne K
authors.initials: RK
authors.lastname: Kunz
authors.forename: David A
authors.initials: DA
authors.lastname: Barda
mesh_terms: D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D013141:Spiro Compounds; C457021:quartromicin