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Steroid Chemistry at a Glance

ISBN: 978-1-119-95729-4
152 pages
June 2011
Steroid Chemistry at a Glance (111995729X) cover image
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

Based on the highly successful and student friendly "at a glance" approach, the information is presented in integrated, self contained double page spreads of text and illustrative material. Students of chemistry and pharmacy using Steroid Chemistry at a Glance will find they have a resource with which they can quickly, concisely and confidently acquire, regularly review and revise the basic facts that underpin the properties, synthesis and reactions of this important class of natural products. It will also serve as a handy bench reference for postgraduates and professional chemists.

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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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          Information is presented in integrated, self contained double page spreads of text and illustrative material

          Layout allows students to quickly, economically and confidently acquire, regularly review and revise the basic facts

          Concise structure details only the essential facts

          Includes a separate Index of Chemical Reactions in addition to the conventional reaction index.

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"Overall, this timely book is a valuable addition to the stable. It is applicable to both chemistry and pharmacy undergraduate curricula, unlocking part of the wealth of chemistry that is the legacy of the great 20th century steroid chemistry effort." (Chemistry World, 1 October 2011)
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