The Search for the Chemistry of Life’s Origin (PDF) 2008
Eidgenössiche Technische Hochschule
Laboratorium für Organische Chemie
Universitätstrasse 16
CH-8092 Zürich (Switzerland)
Deceased Academicians
Most important awards, prizes and academies
Awards: Benoist Prize, Swiss Gov. (1973); Welch Award, R.A. Welch Foundation, Houston, TX (1974); Cope Award, Amer. Chem. Soc. (1984); Wolf Prize in Chemistry, Israel Gov. (1986); Paracelsus Prize, Swiss Chem. Soc. Academies: Akademie der Naturforscher Leopoldina, Halle, Germany; Pontifical Academy of Sciences; Academia Europaea; American Academy of Arts and Sciences, Boston, MA; National Academy of Sciences, Washington, DC; Royal Society, London; Akademie der Wissenschaften, Göttingen, Germany; Croatian Academy of Arts and Sciences. Ordre 'Pour le mérite', Berlin, Germany; Österreichisches Ehrenzeichen für Wissenschaft und Kunst, Wien, Austria.
Summary of scientific research
A. Reaction mechanism and reaction stereochemistry: Early experimental and theoretical studies relevant to terpene biosynthesis on the course and stereochemistry of acid-catalyzed cyclizations of terpenoid polyenes (biogenetic isoprene rule, together with L. Ruzicka, 1953); the stereochemical interpretation of the biogenetic isoprene rule, together with D. Arigoni and L. Ruzicka (1955); the experimental demonstration of strain release control of the oxidation of alcohols with chromic acid (1955) and of stereoelectronic control of SN2- reactions (1970); experimental and theoretical studies on nitrogen inversion (1969). B. Chemical synthesis: development of new reactions and reagents: Introduction of heterocyclic fragmentation reactions into organic synthesis (1952); epoxy-ketone -> alkinone-fragmentation (1967); amide acetal version of Claisen rearrangement (1969); methods for making C, C-bonds: enamino-iminoester condensations (1964), sulfide-contractions (1968), dimethyl-methylidene-iminium iodide (1971) and α-Chloro-nitrone reactions (1972). C. Chemical synthesis: synthesis of complex natural products and related structures: Synthesis of the alcaloid of the autumn crocus, Colchicin (1959); synthetic routes to corrins (1964, 1969); synthesis of vitamin B12 (collaboratively with R.B. Woodward) (1972); synthetic studies related to the problem of vitamin B12biosynthesis (1980). D. Contemporary studies: Chemical etiology of nucleic acid structure; experimental and theoretical studies relevant to the problem of designing chemical models of biogenesis.
Main publications
Eschenmoser, A., Zur säurekatalysierten Zyklisierung bei Mono- und Sesquiterpenverbindungen, Promotionsarbeit Nr 2018, ETH Zürich 1951; Eschenmoser, A., Ruzicka, L., Jeger, O. and Arigoni, D., Zur Kenntnis der Triterpene. Eine stereochemische Interpretation der biogenetischen Isopren regel bei den Triterpenen, Helv. Chim. Acta, 38, p. 1890 (1955); Stadler, P.A., Nechvatal, A., Frey, A.J. and Eschenmoser, A., Untersuchungen über den sterischen Verlauf säurekatalysierter Cyclisationen bei terpenoiden Polyenverbindungen, Helv. Chim. Acta, 40, p. 1373 (1957); Schreiber, J., Leimgruber, W., Pesaro, M., Schudel, P., Threlfall, T. and Eschenmoser, A., Synthese des Colchicins, Helv. Chim. Acta, 44, p. 540 (1961); Bertele, E., Boos, H., Dunitz, J.D., Elsinger, F., Eschenmoser, A., Felner, I., Gribi, H.P., Gschwend, H., Meyer, E.F., Pesaro, M. and Scheffold, R., Ein synthetischer Zugang zum Corrinsystem, Angew. Chem., 76, p. 393 (1964); Felix, D. and Eschenmoser, A., Language Inversion am pyramidal gebundenen Stickstoff: Isolierung von diastereomeren 7-Chlor-7-azabicyclo (4.1.0) heptanen bei Raumtemperatur, Angew. Chem., 80, p. 197 (1968); Yamada, Y., Miljkovic, D., Wehrli, P., Golding, B., Löliger, P., Keese, R., Müller, K. and Eschenmoser, A., Ein neuer synthetischer Zugang zum Corrinsystem, Angew. Chem., 81, p. 301 (1969); Tenud, L., Farooq, S., Seibl, J. and Eschenmoser, A., Endocyclische SN- Reaktionen am gesättigten Kohlenstoff?, Helv. Chim. Acta, 53, p. 2059 (1970); Eschenmoser, A., Roads to Corrins (Centenary Lecture), Quart. Revs., 24, p. 366 (1970); Eschenmoser, A., Post-B12 Problems in Corrin Synthesis, Chem. Soc. Revs., 5, p. 377 (1976); Eschenmoser, A., Organische Naturstoffsynthese heute. Vitamin B12 als Beispiel, Naturwiss, 61, p. 513 (1974), erweiterte Version in Englisch: Eschenmoser, A. and Wintner, C.E., Natural Product Synthesis and Vitamin B12, Science, 196, p. 1410 (1977); Pfaltz, A., Juan, B., Fässler, A., Eschenmoser, A., Jaenchen, R., Gilles, H.H., Diekert, G. and Thauer, R.K., Zur Kenntnis des Faktors F430 aus methanogenen Bakterien: Struktur des porphinoiden Ligandsystems, Helv. Chim. Acta, 65, p. 828 (1982); Eschenmoser, A., Chemistry of Corphinoids, Ann. N.Y. Acad. Sci., 471, p. 108 (1986); Eschenmoser, A., Vitamin B12: Experimente zur Frage nach dem Ursprung seiner molekularen Struktur, Angew. Chem., 100, p. 5 (1988); Eschenmoser, A., Chemical Etiology of Nucleic Acid Structure, Science, 284, p. 2118 (1999).