Steroid Chemistry at a Glance

Introduction.

1 Steroids: a Brief History.

1.1 Structure Determination.

1.1.1 Cholesterol and Cholic Acid.

1.1.2 The Sex Steroids.

1.1.3 Corticosteroids.

2 Sources of Steroids.

2.1 Biosynthesis.

2.2 Commercial Steroid Starting Materials.

2.2.1 Diosgenin.

2.2.2 Soybean Sterols.

3 Estranes: Steroids in Which Ring A is Aromatic.

3.1 Biological Activity.

3.2 Sources of Estranes.

3.2.1 From Androstanes.

3.2.2 Estrogens by Total Synthesis.

3.3 Chemical Reactions of Estranes.

3.3.1 Aromatic A-ring Reactions.

3.3.2 Modifications on Ring B.

3.3.3 Modifications on Ring C.

3.3.4 Modifications on Ring D.

3.4. Some Drugs Based on Estranes.

4 Gonanes or 19-nor-Steroids.

4.1 Preparation of Gonane Starting Materials.

4.1.1 Birch Reduction.

4.1.2 Synthesis by Sequential Annulation Reactions.

4.2 Anabolic–Androgenic Gonanes.

4.2.1 Biological Activity.

4.2.2 Synthesis of 19-Norandrogens.

4.3 Progestational Gonanes.

4.3.1 Biological Activity.

4.3.2 Preparation of 19-Norprogestins.

4.4 Some Drugs Based on Gonanes.

4.4.1 Androgenic–Anabolic Agents.

4.4.2 Progestins.

4.4.3 Progestin Antagonists.

5 Androstanes, C19 Steroids and Their Derivatives.

5.1 Biological Activity.

5.2 Sources of Androstanes.

5.2.1 From Pregnenolone.

5.2.2 Fermentations.

5.2.3 Total Synthesis.

5.3 Modified Anabolic–Androgenic Androstanes.

5.3.1 17-Desalkyl Compounds.

5.3.2 17-Alkyl Compounds.

5.3.3 Modifications on Ring B.

5.3.4 Modifications on Ring C.

5.3.5 Modifications on Ring D.

5.4 17-Spirobutyrolactone Aldosterone Antagonists.

5.5 Some Drugs Based on Androstanes.

5.5.1 Androgens.

5.5.2 Spirobutyrolactones.

6 Pregnanes, Part 1: Progestins.

6.1 Biological Activity.

6.2 Sources of Progesterone.

6.2.1 From Phytochemicals.

6.2.2 By Total Synthesis.

6.2.3 From Dehydroepiandrosterone (DHEA) Acetate.

6.3 Modified Pregnanes.

6.3.1 17-Hydroxy and Acyloxy Derivatives.

6.3.2 Modifications on Ring A.

6.3.3 Modifications on Ring B.

6.3.4 General Methods for Modifications on Ring D.

6.3.5 More Progesterone Analogues.

6.4 Some Drugs Based on Progestins.

6.4.1 Medroxyprogesterone Acetate (10-2).

6.4.2 Megestrol Acetate (10-3).

6.4.3 Melengestrol Acetate (26-7).

7 Pregnanes, Part 2: Corticosteroids.

7.1 Biological Activity.

7.2 Sources of Corticoids.

7.2.1. Introduction of Oxygen at C11.

7.2.2 Construction of the Dihydroxyacetone Side Chain.

7.3 Modified Corticoids.

7.3.1 Unsaturation.

7.3.2 Additional Alkyl Groups.

7.3.3 Halogenated Corticoids.

7.3.4 Hydroxylation: 16,17-Diols.

7.3.5 Corticoids with Multiple Modifications.

7.3.6 Miscellaneous Corticoids.

7.4 Some Drugs Based on Corticoids.

8 Miscellaneous Steroids.

8.1 Heterocyclic Steroids.

8.1.1 Introduction.

8.1.2 Steroids with a Heteroatom in Ring A.

8.1.3 Steroids with a Heteroatom in Ring B.

8.1.4 Steroids with a Heteroatom in Ring C.

8.1.5 Steroids with a Heteroatom in Ring D.

8.2 Cardenolides.

8.2.1 Actodigin Aglycone.

8.2.2 Synthesis from a Bile Acid.

8.3 Compounds Related to Cholesterol.

Subject Index.

Reactions Index.