Question

(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3, 17-dione, also called “andro,” from the following description. Andro contains the tetracyclic steroid with carbonyl groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10 and C13.

(b) Add wedges and dashed wedges for all stereogenic centers with the following information: the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are trans to each other.

Short answer

Answer

(a.)

(b.)

Step-by-step solution

Steroid structure

Steroid structure consists of one 5-membered ring joined by three 6-membered rings.There are angular methyl groups attached to steroids, and all rings in steroids are transfused.

Skeletal structure of anabolic steroid 4-androstene-3, 17-dione

Given that andro contains tetracyclic steroid, it means four cyclic rings. The methyl groups are bonded to C10 and C13. The carbonyl groups are connected to C3 and C17. One double bond is present between C4 and C5.

Skeletal structure of anabolic steroid 4-androstene-3, 17-dione

Wedges and dashed wedges of anabolic steroid 4-androstene-3, 17-dione

At C10, the configuration is R, and at C13, the configuration is S.

Wedge and dashed wedges bonds