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.
[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.
Roush
William R
WR
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA. roush@umich.edu
Limberakis
Chris
C
Kunz
Roxanne K
RK
Barda
David A
DA
D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D005663:Furans; D013141:Spiro Compounds; C457021:quartromicin