Stereoselective Michael addition of carbon-, nitrogen-, oxygen-, and sulfur-centered nucleophiles on enantiopure hydroxylated 6,7-dehydro-5-oxoindolizidine. Synthesis of carbon- or hetero-7-substituted swainsonine analogues.
Enantiopure alpha,beta-unsaturated delta-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines: (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.
Tinarelli
Alessandro
A
Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy.
Paolucci
Claudio
C
D002244:Carbon / Q000737:chemistry*; D006900:Hydroxylation; D007212:Indolizines / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D017026:Swainsonine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*
C520381:6,7-dehydro-5-oxoindolizidine; D007212:Indolizines; D013455:Sulfur; D002244:Carbon; D009584:Nitrogen; D017026:Swainsonine; D010100:Oxygen