Stereoselective synthesis of 9alpha-hydroxylated ecdysteroids.
Treatment of ecdysteroids with excess of TBAF in THF was shown to proceed with stereoselective oxidation at the 9alpha position of the carbon skeleton. The stereochemistry of the products was confirmed by X-ray analysis. Using this method, 9alpha-hydroxyecdysteroids were obtained in good yield. The results open a route to novel type of natural and modified steroids that are difficult to access otherwise.
Drach
Svetlana V
SV
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Laboratory of Steroid Chemistry, Kuprevich St. 5/2, 220141 Minsk, Belarus.
Khripach
Vladimir A
VA
Litvinovskaya
Raisa P
RP
Lyakhov
Alexander S
AS
Schneider
Bernd
B
Zhylitskaya
Halina A
HA
D018360:Crystallography, X-Ray; D026461:Ecdysteroids / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D026461:Ecdysteroids