Steroid Chemistry at a Glance

The term steroid has become virtually synonymous with drug abuse in sport to the majority of the public. However these steroids - androgens - actually comprise only a single relatively small class of biologically active steroids, and are overshadowed by a large collection of compounds, a sizeable number of which are commercial drugs that share the same structural carbon skeleton. The development of these drugs has led to a large body of organic chemistry often denoted as "Steroid Chemistry". Steroid Chemistry At A Glance provides a concise overview of the main principles and reactions of steroid chemistry. Topics covered include: history, isolation and structure determination of steroids steroid nomenclature and stereochemistry natural sources of steroids synthesis and reactions of aromatic a-ring steroids, androstanes, and pregnanes steroids with a spirolactone at position 17 steroids with hetrocyclic ring A compounds derived from cholesterol &l

Dr Daniel Lednicer's career in both the private and public sectors has been devoted to the search for new therapeutic agents. Dr. Lednicer spent two decades at the bench as a chemist at the Upjohn Company. Following that, he served as director of chemical research at Mead Johnson, director of pharmaceutical sciences at Adria Laboratories, and pharmaceutical manager at Analytical Biochemistry Laboratories. Most recently, he was a project officer at the National Cancer Institute. Dr Lednicer is the acclaimed author of several books on drug synthesis and discovery, including 7 volumes of the series Organic Chemistry of Drug Synthesis (Wiley US).

Preface.

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.

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Steroid Chemistry at a Glance

Summary

Author Biography

Table of Contents

Supplemental Materials