Blickenstaff / Ghosh / Wolf Total Synthesis of Steroids

Organic Chemistry: A Series of Monographs, Vol. 30
1. Auflage 2013
ISBN: 978-1-4832-1642-3
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, 344 Seiten, Web PDF

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, 3á-hydroxy-5a-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.

Autoren/Hrsg.

Blickenstaff, Robert T.

Ghosh, Anil C.

Wolf, Gordon C.

Blomquist, Alfred T.

Wasserman, Harry

Inhaltsverzeichnis

1;Front Cover;1
2;Total Synthesis of Steroids;4
3;Copyright Page;5
4;Table of Contents;8
5;Dedication;6
6;Preface;12
7;Abbreviations;14
8;Chapter 1. Designing Total Syntheses;16
8.1;1.1 Introduction;16
8.2;1.2 Defining the Problem;18
8.3;1.3 Methods and Reactions;25
8.4;1.4 Resolutions;38
8.5;References;44
9;Chapter 2. Biogenetic-like steroid Synthesis;50
9.1;2.1 Cyclization of Terminal Epoxides;52
9.2;2.2 Total Synthesis from Nonepoxide Precursors;56
9.3;References;61
10;Chapter 3. AB->ABC->ABCD;64
10.1;3.1 Equilenin;64
10.2;3.2 Estrone;73
10.3;3.3 Bisdehydrodoisynolic Acid;78
10.4;3.4 18,19-Bisnorprogesterone and 19-Norpregnanes;80
10.5;3.5 Miscellaneous Syntheses;83
10.6;3.6 Heterocyclic Steroids;86
10.7;References;94
11;Chapter 4. AB +D->ABD-> ABCD;100
11.1;4.1 Introduction;100
11.2;4.2 The Torgov Synthesis;101
11.3;4.3 Alkylation;118
11.4;4.4 Michael Addition;120
11.5;4.5 Enamines;123
11.6;4.6 Acylation;125
11.7;4.7 Aldol-Type Condensations;126
11.8;4.8 Organometallic Coupling;130
11.9;4.9 Miscellaneous Methods;133
11.10;References;133
12;Chapter 5. AB + D ->ABCD;141
12.1;5.1 Introduction;141
12.2;5.2 Carbocyclics;142
12.3;5.3 Thiasteroids;146
12.4;References;146
13;Chapter 6. A+C ->ABC -> ABCD;149
13.1;6.1 Synthesis from p-Anisylcyclohexanes;149
13.2;6.2 Synthesis from C-5, C-8 Bridged Intermediates;152
13.3;References;155
14;Chapter 7. A+CD -> ACD ->ABCD;157
14.1;7.1 Condensation of Ring-A Anionic Fragments with CD Ketones;157
14.2;7.2 Alkylation of an Anionic CD Fragment;161
14.3;7.3 The Wittig Reaction in Total Synthesis;166
14.4;7.4 CD Enamine Intermediates;167
14.5;7.5 Thiasteroids;169
14.6;7.6 Miscellaneous Routes;171
14.7;References;173
15;Chapter 8. A+D -> AD ->ABCD;176
15.1;8.1 The Smith-Hughes Approach;176
15.2;8.2 8-Azasteroids;181
15.3;8.3 8,13-Diazasteroids;184
15.4;8.4 Miscellaneous Routes;185
16;Chapter 9. BC ->ABC ->ABCD;191
16.1;9.1 Synthesis of Epîandrosterone;191
16.2;9.2 Other Methods;195
16.3;9.3 Synthesis According to Wilds;196
16.4;9.4 Synthesis of Cortisone;197
16.5;9.5 Synthesis of Aldosterone;202
16.6;9.6 3/ß-Hydroxy-5a:-pregnan-20-one? Latifoline, and Conessine;209
16.7;9.7 Ring-C Aromatic Steroids;211
16.8;References;211
17;Chapter 10. BC -> BCD ->ABCD;216
17.1;10.1 Introduction;216
17.2;10.2 Trans-Benzohydrindane Derivatives;217
17.3;10.3 19-Nortestosterone;218
17.4;10.4 Adrenocortical Steroids;221
17.5;10.5 Estrogens;221
17.6;10.6 10-Allyl Steroids;222
17.7;10.7 19-Norprogesterone and 11-Hydroxy Steroids;223
17.8;10.8 Trienes;226
17.9;10.9 7a-Methyl Steroids;228
17.10;10.10 Miscellaneous Steroidal Derivatives;228
17.11;10.11 Isosteroids;233
17.12;10.12 11-Oxygenated Steroids and Conessine;237
17.13;10.13 Miscellaneous Synthetic Routes;241
17.14;References;243
18;Chapter 11. B+D ->BD ->BCD ->ABCD;249
18.1;References;253
19;Chapter 12. CD -> BCD -> ABCD;254
19.1;12.1 CD Intermediates;254
19.2;12.2 Hydrochrysene Approach;258
19.3;12.3 Modifications of the Hydrochrysene Synthesis;269
19.4;12.4 C-Nor-D-homosteroids;271
19.5;12.5 Woodward Synthesis;275
19.6;12.6 Asymmetric Induction;281
19.7;12.7 Hoffmann-LaRoche Approach;288
19.8;12.8 Miscellaneous Syntheses;290
19.9;References;294
20;Appendix: Supplementary References;301
20.1;Chapter 1. Designing Total Syntheses;301
20.2;Chapter 2. Biogenetic-like Steroid Synthesis;302
20.3;Chapter 3. AB ->ABC -> ABCD;302
20.4;Chapter 4. AB + D -> ABD -> ABCD;303
20.5;Chapter 5. AB + D -> ABCD;304
20.6;Chapter 8. A + D -> AD -> ABCD;305
20.7;Chapter 9. BC -> ABC -> ABCD;306
20.8;Chapter 10. BC ->BCD -> ABCD;306
20.9;Chapter 11. B+D -> BD -> BCD -> ABCD;306
20.10;Chapter 12. CD -> BCD -> ABCD;306
21;Author index;308
22;Subject index;332