The biological effects of a series of 13β-substituted gonanes related to norethisterone 1817α-ethynyl-19-nortestosterone)

Structural requirements for progestational activity. Synthesis and properties of rac-8.alpha.,9.beta.,10.alpha.14.beta.-progesterone

“…(C) A solution of 0.15 g of 7a in 10 mL of anhydrous pyridine plus 1 mL of acetic anhydride was stirred at room temperature for 12 h. Standard workup afforded the acetate 7c as a gum sufficiently pure for further reaction: NMR (CDC13) 0.87 (s, C-19 H's), 2.03 (s, acetate H's), 2.24 (s, C-21 H's), 4.71 (m, C-3d H).…”

“…A single crystal taken from rac-1 was determined to be in space group P212121, which indicates that the crystal contains only one enantiomer. The unit cell constants were determined from a leastsquares analysis of the 0 values for 32 reflections to be a - 12.8727 (8), b = 17.957 (1), and c = 7.5684 (5) Á resulting in a unit cell volume of 1750 A3. The density was calculated to be 1.19 g cm 3 based on the presence of four molecules (Z = 4), each of molecular weight 314.47, in the cell.…”

Steroidal estrogens

“…A number of derivatives of estrone have been synthesized by further modification of the starting substances (71,119,121,128,189,190,386,387), and elaboration of the intermediates (L, LV, and LVII) gave five of the stereoisomers of estrone. priate tetralone (295), could be condensed with 2-methylcyclohexane-1,3-dione (LXIII) (see Chart VI) in the presence of a base to give a 50% yield of dione LXV.…”

Synthesis of 11.beta.,13.beta.- and 13.beta.,16.beta.-propano steroids: probes of hormonal activity

“…The conformation of the C-13 substituent in these steroids is rigidly defined and skeletal distortions due to nonbonded interactions of the C-13/3 substituent with the C-ll/3 and C-16/3 substituents are eliminated. The starting point for both of these bridge systems was 17/3-hydroxy-3-methoxy-13/3-(3'-phenoxypropyl)gona-l,3,5 (10),8-tetraene (1), obtained by our recently reported procedure. 4 Chemistry.…”