Synthesis of novel steroidal D-ring substituted isoxazoline derivatives of 17-oxoandrostanes.
A facile synthesis of isoxazoline derivatives of 17-oxoandrostane at the side chain of D-ring is reported. The scheme involves the transformation of the starting dehydroepiandrosterone acetate (ketone) to the Knoevenegel product, reduction to the nitrile, and elimination to the carboxaldehyde. Cycloaddition of nitrileoxides across olefinic aldehyde intermediate led to the synthesis of novel side chain isoxazoline derivatives.
Banday
Abid H
AH
Synthetic Chemistry Division, Indian Institute of Integrative Medicine, Jammu Tawi, India.
Singh
Swarn
S
Alam
M Sarwar
MS
Reddy
Doma M
DM
Gupta
B D
BD
Sampath Kumar
H M
HM
D000731:Androstanes / Q000138:chemical synthesis / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000731:Androstanes; D006571:Heterocyclic Compounds; D007555:Isoxazoles