
TY  - JOUR
A1  - Cambie, RC 
A1  - Potter, GJ 
A1  - Read, RW 
A1  - Rutledge, PS 
A1  - Woodgate, PD 
T1  - Solanum alkaloids. XVIII. Utilization of solasodine for the preparation of nitrogen analogues of ecdysones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1981
VL  - 34
IS  - 3
SP  - 599
EP  - 622
KW  - 
UR  - https://doi.org/10.1071/CH9810599 
N2  - 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. 
ER  -

