6533b7d7fe1ef96bd12682b8
RESEARCH PRODUCT
Auxiliary-controlled stereoselective enolate protonation: Enantioselective synthesis of cis and trans annulated decahydroquinoline alkaloids
Horst KunzMarkus WeymannMartin Schultz-kukulasubject
Bicyclic moleculeStereochemistryOrganic ChemistryEnantioselective synthesisProtonationBiochemistrychemistry.chemical_compoundPumiliotoxin CchemistryDrug DiscoveryStereoselectivityEnoneCis–trans isomerismConjugatedescription
Abstract The diastereoselective synthesis of the octahydroquinoline enone precursor of pumiliotoxin C is achieved via tandem Mannich-Michael reaction on N-galactosyl imines. Conjugate cuprate addition to the bicyclic enone stereoselectively forms the trans annulated 4a- epi -pumiliotoxin C skeleton in the presence of the carbohydrate auxiliary, and the cis annulated pumiliotoxin C skeleton in its absence.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1998-10-01 | Tetrahedron Letters |