(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 skeleton 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.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.22P
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(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 skeleton 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.

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