A synthetic approach to the Stemona alkaloids.
This paper describes our work developing a strategy for the construction of the typical core structure of the Stemona alkaloids. The approach is to control the relative stereochemistry of the groups on the core 1-azabicyclo[5.3.0]decane ring system by a [3,3] sigmatropic rearrangement of an acylimmonium ion followed by selective reduction. After optimization, this reaction sequence afforded the desired diastereomer in 62% yield. Further efforts were directed toward elaboration of the characteristic butyrolactone substituent.
Hinman
M M
MM
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Heathcock
C H
CH
D000470:Alkaloids / Q000138:chemical synthesis*; D019684:Magnoliopsida / Q000737:chemistry*
D000470:Alkaloids