1.
J Org Chem
; 66(23): 7751-6, 2001 Nov 16.
Article
in English
| MEDLINE
| ID: mdl-11701032
ABSTRACT
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.