6533b7dcfe1ef96bd1271d98
RESEARCH PRODUCT
Carbohydrate Auxiliaries in Stereoselective Syntheses of Decahydroquinoline Alkaloids
Horst KunzMartin Schulz-kukulaStephan KnauerMarkus Weymannsubject
Chiral auxiliarychemistry.chemical_compoundchemistryStereochemistryEnantioselective synthesisOrganic chemistryStereoselectivityProtonationEnantiomerCarbohydrateConjugatedescription
Using tetra-O-pivaloyl-β-D-galactopyranosylamine as the chiral auxiliary, both trans- and cis-annelated decahydroquinoline alkaloids can be synthesized stereoselectively. This methodology of asymmetric synthesis is based on the effect that both enantiomers of 2,6-disubstituted piperidin-4-ones are selectively and alternatively accessible using the auxiliary as the identical stereodifferentiating tool. In addition, the carbohydrate auxiliary controls the stereoselective protonation of enolates formed by conjugate addition of cuprates to N-galactosyl octahydroquinolin-4-ones. The syntheses of trans-4a-epi-pumiliotoxin C and cis-4a-epi-perhydro-219A illustrate this concept of asymmetric synthesis of decahydroquinoline alkaloids.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-01-01 |