Synthesis of precursors of the agalacto (exo) fragment of the quartromicins via an auxiliary-controlled exo-selective Diels-Alder reaction.
[reaction: see text] A direct synthesis of the alpha-hydroxyaldehyde exo-5, a precursor of the exo-spirotetronate subunit of the quartromicins, was achieved through an exo-selective Lewis acid-catalyzed Diels-Alder reaction of dienophile 12a and diene 1.
Qi
Jun
J
Department of Chemistry, University of Michigan, Ann Arbor, 48109, USA.
Roush
William R
WR
D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D013141:Spiro Compounds; C457021:quartromicin