
%0 Journal Article
%A Cambie, RC 
%A Potter, GJ 
%A Read, RW 
%A Rutledge, PS 
%A Woodgate, PD 
%T Solanum alkaloids. XVIII. Utilization of solasodine for the preparation of nitrogen analogues of ecdysones
%J Australian Journal of Chemistry
%D 1981/03/01
%V 34
%N 3
%P 599-622
%K 
%R https://doi.org/10.1071/CH9810599
%U https://www.publish.csiro.au/paper/CH9810599 
%X Solasodine (spirosol-5-en-3&#946;-01) (1) has been converted into (20S,22R,25R)-26-acetylamino-2&#946;,3&#946;,14&#945;- trihydroxy-5&#946;-furost-7-en-6-one (41), a compound bearing ecdysone functionality in the steroidal nucleus aud retaining the N-atom in the side chain. The route involves dehalogenation of the bromohydrin (19), formed by treatment of N,O-diacetylsolasodine (6) with N-bromoacetamide and perchloric acid as catalyst. The 2&#946;-, 3&#946;- and 14&#945;-hydroxy groups are introduced by Woodward-Prévost and selenium dioxide oxidations, respectively. 
