Total Synthesis of Steroids - 1st Edition - ISBN: 9780121059507, 9781483216423

Total Synthesis of Steroids

1st Edition

Organic Chemistry: A Series of Monographs, Vol. 30

Authors: Robert T. Blickenstaff Anil C. Ghosh Gordon C. Wolf
Editors: Alfred T. Blomquist Harry Wasserman
eBook ISBN: 9781483216423
Imprint: Academic Press
Published Date: 28th January 1974
Page Count: 344
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Organic Chemistry, Volume 30: Total Synthesis of Steroids provides an overall view of steroid total synthesis, including the general approaches, special problems, stereochemical complexities, expansion or contraction of rings, and insertion of hetero atoms. The book discusses the process of designing total syntheses; the biogenetic-like steroid synthesis, including cyclization of terminal epoxides as well as the total synthesis from nonepoxide precursors; and the synthesis of equilenin, estrone, bisdehydrodoisynolic acid, 18,19-bisnorprogesterone, 19-norpregnanes, and heterocyclic steroids. The text also describes the application of ABD intermediates in the Torgov synthesis; the synthesis of carbocyclics and thiasteroids; and the synthesis from p-anisylcyclohexanes and from C-5, C-8 bridged intermediates.
The synthesis based on the type of reaction used in the condensation of the A fragment with the CD portion, as well as the methods of total synthesis in the preparation of 8-azasteroids and 8,13-diazasteroids are also considered. The book further tackles the synthesis of epiandrosterone, cortisone, aldosterone, 3β-hydroxy-5α-pregnan-20-one, latifoline, conessine, and ring C aromatic steroids; the synthesis of trans-benzohydrindane derivatives and other common derivatives; and the synthesis of CD intermediates. Chemists, biochemists, and people involved in the study of steroid total syntheses will find the book invaluable.

Table of Contents

Preface Abbreviations

  1. Designing Total Syntheses 1.1 Introduction 1.2 Defining the Problem 1.3 Methods and Reactions 1.4 Resolutions References
  2. Biogenetic-like Steroid Synthesis 2.1 Cyclization of Terminal Epoxides 2.2 Total Synthesis from Nonepoxide Precursors References
  3. AB → ABC → ABCD 3.1 Equilenin 3.2 Estrone 3.3 Bisdehydrodoisynolic Acid 3.4 18,19-Bisnorprogesterone and 19-Norpregnanes 3.5 Miscellaneous Syntheses 3.6 Heterocyclic Steroids References
  4. AB + D → ABD → ABCD 4.1 Introduction 4.2 The Torgov Synthesis 4.3 Alkylation 4.4 Michael Addition 4.5 Enamines 4.6 Acylation 4.7 Aldol-Type Condensations 4.8 Organometallic Coupling 4.9 Miscellaneous Methods References
  5. AB + D → ABCD 5.1 Introduction 5.2 Carbocyclics 5.3 Thiasteroids References
  6. A + C → AC → ABC → ABCD 6.1 Synthesis from p-Anisylcyclohexanes 6.2 Synthesis from C-5,C-8 Bridged Intermediates References
  7. A + CD → ACD → ABCD 7.1 Condensation of Ring-A Anionic Fragments with CD Ketones 7.2 Alkylation of an Anionic CD Fragment 7.3 The Wittig Reaction in Total Synthesis 7.4 CD Enamine Intermediates 7.5 Thiasteroids 7.6 Miscellaneous Routes References
  8. A + D → AD → ABCD 8.1 The Smith-Hughes Approach 8.2 8-Azasteroids 8.3 8,13-Diazasteroids 8.4 Miscellaneous Routes References
  9. BC → ABC → ABCD 9.1 Synthesis of Epiandrosterone 9.2 Other Methods 9.3 Synthesis According to Wilds 9.4 Synthesis of Cortisone 9.5 Synthesis of Aldosterone 9.6 3β-Hydroxy-5α-pregnan-20-one, Latifoline, and Conessine 9.7 Ring-C Aromatic Steroids References
  10. BC → BCD → ABCD 10.1 Introduction 10.2 Trans-Benzohydrindane Derivatives 10.3 19-Nortestosterone 10.4 Adrenocortical


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© Academic Press 1974
Academic Press
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About the Author

Robert T. Blickenstaff

Anil C. Ghosh

Gordon C. Wolf

About the Editor

Alfred T. Blomquist

Harry Wasserman

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