Total synthesis of (-)-aurantioclavine.
The concise total synthesis of (-)-aurantioclavine has been achieved by taking advantage of strategies for the asymmetric alkenylation of N-tert-butanesulfinyl imines. The enantiomerically pure natural product was prepared in 6 steps and 27% overall yield by using Rh-catalyzed addition of a N-methyliminodiacetic acid (MIDA) boronate and in 5 steps and 29% yield by employing a Grignard reagent addition sequence.
Brak
Katrien
K
University of California-Berkeley, Department of Chemistry, Berkeley, California 94720, USA.
Ellman
Jonathan A
JA
D004876:Ergot Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004876:Ergot Alkaloids; C551152:aurantioclavine