Prizes are Good but Discoveries are Better
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Eschenmoser, A. (2025). Prizes are Good but Discoveries are Better. GNT Publishing GmbH. https://doi.org/10.47261/1569
Eschenmoser, Albert. Prizes are Good but Discoveries are Better. GNT Publishing GmbH, 2025. Book. https://doi.org/10.47261/1569
Eschenmoser, A (2025): Prizes are Good but Discoveries are Better, GNT Publishing GmbH, [online] https://doi.org/10.47261/1569
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Prizes are Good but Discoveries are Better
Lives in Chemistry – Lebenswerke in der Chemie, Vol. 13
(2025)
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Abstract
ALBERT ESCHENMOSER (1925-2023), the brilliant Swiss chemist quietly composed an autobiography describing his six professional decades just »for the sake of its existence.«Already as a PhD student at ETH Zurich, he discerned patterns in the biogenesis of terpenes. His passion for synthesis of very complex molecules culminated in the world famous »competitive collaboration“ with R.B. Woodward’s group resulting in two total syntheses of Vitamin B12.Albert Eschenmoser asked questions like »How did life on Earth arise? Why did Nature choose the biomolecules we know?« Clearly his vision went beyond synthesis - he pondered about fundamental issues following his conviction: »Life: perfectly commonplace and an everlasting miracle at the same time. Its emergence about four billion years ago … is the most significant chemical property of matter«.This reflects Eschenmoser’s unique stature among 20th century scientists.l-i-c.org/1136
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Lives in Chemistry | 3 | ||
| Imprint | 6 | ||
| Table of Contents | 8 | ||
| Preface | 11 | ||
| 1 From Primary School to ETH (1932–1951) | 17 | ||
| 1.1 Undergraduate studies | 20 | ||
| 1.2 Military service | 26 | ||
| 1.3 Student life | 28 | ||
| 1.4 Diploma thesis and diploma | 30 | ||
| 1.5 Zingiberene structure | 34 | ||
| 1.6 Farnesene Rule | 37 | ||
| 1.7 Jakob Schreiber, my first student | 42 | ||
| 1.8 Hans Schinz, my doctoral thesis supervisor | 44 | ||
| Footnotes | 46 | ||
| 2 From Postdoc to Privatdozent at ETH (1951–1960) | 49 | ||
| 2.1 Founding the Eschenmoser group | 51 | ||
| 2.2 Steroid syntheses | 54 | ||
| 2.3 Base-induced fragmentation of C,C bonds | 58 | ||
| 2.4 Biogenetic Isoprene Rule | 59 | ||
| 2.5 Stereochemistry of acid-catalyzed polyene cyclizations | 64 | ||
| 2.6 Stereochemical interpretation of the Biogenetic Isoprene Rule in triterpenes | 66 | ||
| 2.7 First trip to the USA (1954) | 70 | ||
| 2.8 Edgar Heilbronner and the benzotropylium cation | 75 | ||
| 2.9 Determination of the relative configuration of secondary alicyclic alcohols | 77 | ||
| 2.10 Total synthesis of colchicine | 79 | ||
| Desacetylamino-colchicine | 87 | ||
| 2.11 Laboratory of Organic Chemistry: from Ruzicka to Prelog | 89 | ||
| Harlan Goering | 91 | ||
| Footnotes | 93 | ||
| 3 Professor at ETH—Reaction Mechanisms and Syntheses (1960–1992) | 97 | ||
| 3.1 Courses and lectures at home and abroad | 99 | ||
| 3.2 Visiting professor at MIT (1961) | 101 | ||
| 3.3 Visiting professor at University of Wisconsin (1965) | 103 | ||
| 3.4 Turbulent times at ETH | 105 | ||
| 3.5 The corrin saga and the synthesis of vitamin B₁₂ (1960–1972) | 112 | ||
| IUPAC International Symposium on the Chemistry of Natural Products (1960) | 115 | ||
| Model-corrin synthesis (1964) | 117 | ||
| Vitamin B₁₂ synthesis—ring-B precursor | 127 | ||
| The dream of a vitamin B₁₂ synthesis from a single starting material | 129 | ||
| Vitamin B₁₂ synthesis—ring-C precursor | 129 | ||
| Synthesis of the B-C component | 130 | ||
| Transatlantic cooperation - phase I | 133 | ||
| Model-corrin synthesis 1968—photochemical A/D-secocorrin→corrin cycloisomerization | 139 | ||
| The common corrinoid intermediate via photochemical A/D-secocorrin→corrin cycloisomerization | 146 | ||
| Transatlantic cooperation—phase II | 152 | ||
| Black Friday | 154 | ||
| Jointly executed final steps to cobyric acid | 155 | ||
| 3.6 Post-B₁₂ psychological and publication issues (1973–1992) | 164 | ||
| Promises—not kept | 168 | ||
| 3.7 Research topics also running I (1960–1972) | 169 | ||
| α,β-Epoxyketone to alkynone fragmentation | 169 | ||
| Non-existence of endocyclic SN2-type reactions | 170 | ||
| Chemistry of vinyl nitrosonium salts | 173 | ||
| Slow nitrogen inversion in tertiary amines | 173 | ||
| N,N-Dimethyl-N-methylidene immonium iodide | 175 | ||
| Footnotes | 177 | ||
| 4 Professor at ETH—Etiologies and Prebiotics (1973–2008) | 183 | ||
| 4.1 Chemical etiology of the vitamin B₁₂ structure (1973–1988) | 185 | ||
| Do dark variants of the A/D-secocorrin→corrin cycloisomerization exist? | 185 | ||
| The 20-methyl-20-hydroxy-dihydrocorphinate→19-acetyl-corrinate ring contraction | 186 | ||
| Is the apparently complex molecular structure of vitamin B₁₂ in fact a simple one? | 189 | ||
| Arrangement of the peripheral acetic and propionic acid side chains on the corrin ring | 190 | ||
| Why is vitamin B₁₂ a corrin and not a corphin? | 191 | ||
| Why is the nucleotide chain of vitamin B₁₂ linked to the propionic acid side chain of ring D? | 193 | ||
| How and why is the periphery of the four five-membered rings of vitamin B₁₂ quaternized by C-methyl | 195 | ||
| Some social-scientific collaterals from the times of the B₁₂ etiology | 196 | ||
| 4.2 Research topics also running II (1973–1988) | 197 | ||
| A new corphinoid coenzyme: Factor F430 | 197 | ||
| The question of the structure of the photosynthetic reaction center P700 | 199 | ||
| Fragmentative access to macrolides | 201 | ||
| Stereochemistry of allylic reactions | 202 | ||
| 4.3 Prebiotics (1976–2008) | 202 | ||
| 4.4 Etiology of the structural type of natural nucleic acids (1987–2008) | 211 | ||
| Oligo-dipeptamidines | 212 | ||
| Why pentose and not hexose nucleic acids? | 213 | ||
| Homo-DNA | 216 | ||
| Gluco-, allo-, and altropyranose oligonucleotides | 218 | ||
| Pyranosyl-RNA: D-β-ribo-pyranosyl-(2’→4’)-oligonucleotides | 220 | ||
| Self-assembly of p-RNA duplexes | 222 | ||
| On the origin of biological homochirality | 223 | ||
| Xylo-, lyxo-, and arabinopyranose isomers of p-RNA | 225 | ||
| TNA: L-α-threo-furanosyl-(2’→3’)-oligonucleotides | 225 | ||
| Footnotes | 232 | ||
| 5 Emeritus | 233 | ||
| 5.1 University of Frankfurt (1993 - 1996) | 241 | ||
| 5.2 The Scripps Research Institute (1996 - 2009) | 243 | ||
| Prehistory of an extraordinary privilege | 243 | ||
| Everyday life in La Jolla | 246 | ||
| Research at TSRI | 248 | ||
| Footnotes | 254 | ||
| 6 Other Activities and Honors | 255 | ||
| 6.1 Consulting | 257 | ||
| Fluka | 257 | ||
| Ciba | 258 | ||
| Firmenich | 259 | ||
| 6.2 Lecture tours and symposia | 260 | ||
| 6.3 Visiting professorships | 269 | ||
| 6.4 Membership in academies | 271 | ||
| 6.5 Awards | 272 | ||
| Footnotes | 276 | ||
| Concluding Remarks | 277 | ||
| How this autobiography came about: the backstory | 279 | ||
| Post-La Jolla activities | 284 | ||
| Acknowledgements | 286 | ||
| Appendix | 287 | ||
| Biographical notes | 289 | ||
| Footnotes | 312 | ||
| Vita | 313 | ||
| Chemistree | 314 | ||
| Holographs | 316 | ||
| References | 320 | ||
| Table of contents | 334 | ||
| Links and literature | 339 | ||
| Image sources | 341 | ||
| Index | 342 | ||
| Reactions / The Series | 349 |