Enantiopure a,b-unsatd. d-lactams I (R = H or OH) react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate addns. is demonstrated through the synthesis of two new substituted indolizidines:(7R)-7-amino-8-deoxyswainsonine and (7R)-7-acetylaminoswainsonine.
A. Tinarelli, C. Paolucci (2006). tereoselective 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. JOURNAL OF ORGANIC CHEMISTRY, 71, 6630-6633 [10.1021/jo060511p].
tereoselective 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.
PAOLUCCI, CLAUDIO
2006
Abstract
Enantiopure a,b-unsatd. d-lactams I (R = H or OH) react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate addns. is demonstrated through the synthesis of two new substituted indolizidines:(7R)-7-amino-8-deoxyswainsonine and (7R)-7-acetylaminoswainsonine.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
