1, 4-diène-stéroïdes et leur procédé de fabrication

摘要

1,192,062. #1,4 - 3 - Hydroxysteroids. AMERICAN HOME PRODUCTS CORP. 24 April, 1967 [13 March, 1967], No. 63268/69. Divided out of 1,192,061. Heading C2U. The invention comprises compounds of formula wherein R is C 1-5 alkyl; R1, R2 and R3 are H or C 1-5 alkyl; and X is a radical selected from wherein R4 is H or C 1-5 alkyl; A is protected carbonyl or C(α-R6)(#-OH) where R6 is a C 1-5 alkyl, alkenyl, alkynyl or chloroalkynyl group; B is CH 2 , CHOH or protected carbonyl; provided that when B is CH 2 , A is C(α-R6)(#-OH) where R6 is C 2-5 alkyl, and that when B is CHOH, A is protected carbonyl or C(α-R6)- (#-OH) where R6 is C 2-5 alkyl; and wherein R4 and B are as above; D is CH 2 , CHOH or CHF; R7 is H(OH) or protected carbonyl; R8 and R9 are each H, OH or protected OH; R10 is H or C 1-5 alkyl; and R11 is H or F; provided that when B is CHOH, D is CH 2 and R7 is H(OH) then R8 and R9 are each H or protected OH, and that when B is CHOH, D is CH 2 and R7 is protected carbonyl then R8 and R9 are both H. These compounds are prepared by reduction of the corresponding 1,4-dien-3-ones using aluminium hydride or a complex aluminium hydride at a temp. below 10‹ C. The products may be acylated.