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The History of Synthetic Organic Chemistry: A Journey from Urea to Taxol


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1 Department of Chemistry, Dr. Sudhir Chandra Sur Institute of Technology and Sports Complex, JIS Group of College, 540 Dum Dum, Kolkata-700074, India
     

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Synthetic Organic Chemistry is the backbone in modern Science. Nowadays, Organic Chemists are in such a triumph position that any complicated, bulky, stereo-chemically enriched and highly strained molecule can be synthesized very easily and within very short period of time. In 1828, German Chemist F. Wöhler first reported the synthesis of an Organic molecule namely, Urea from ammonium cyanate in his laboratory without any aid of microorganism. From that day, the journey of synthesis started. Then, Woodward introduced the method of how to synthesize targeted molecules by proper planning via retro-synthetic approach. Presently, Synthesis of Taxol (anti-cancer drug) can be achieved very smoothly in laboratory.

Keywords

History, synthetic, organic, chemistry, urea, taxol, natural products.
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  • F Wöhler, Ueber künstliche Bildung des Harnstoffs, Ann. Chim. Phys., Vol 88, No 2, page 253-256, 1828.(doi.org/10.1002/andp.18280880206)

  • K C Nicolaou, Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory, Proceeding of Royal Society A, Vol 470, page 2163, 2014. (doi.org/10.1098/rspa.2013.0690)

  • H Kolbe, Beiträge zur Kenntniss der gepaarten Verbindungen, Justus Liebigs Annalen der Chemie, Vol 54, No 2, page 145–188, 1845. (doi.org/10.1002/jlac.18450540202)

  • C Graebe and C Liebermann, Ueber künstliche Bildung von Alizarin, Berichte der deutschen chemischen Gesellschaft, Vol 2, No 1, page 14, 1869. (doi.org/10.1002/cber.18690020106)

  • A Baeyer and V Drewsen, Darstellung von Indigblau aus Orthonitrobenzaldehyd, Berichte der deutschen chemischen Gesellschaft, Vol 15, No 2, page 2856-2864, 1882. (doi.org/10.1002/cber.188201502274)

  • J Wilbrand, Notiz über Trinitrotoluol, Justus Liebigs Annalen der Chemie, Vol 128, No 2, page 178-179, 1863. (doi:10.1002/jlac.18631280206)

  • C Häussermann, Über die explosiven Eigenschaften des Trinitrotoluols, Angewandte Chemie, Vol 4, No 17, page 508-511, 1891. (doi.org/10.1002/ange.18910041703)

  • E Fischer, Synthese des Traubenzuckers, Berichte der deutschen chemischen Gesellschaft, Vol 23, No 1, page 799-805, 1890. (doi:10.1002/cber.189002301126)

  • G F Henning, Patent No. DE104280, 1899.

  • M Tswett, Physikalisch-chemische Studien über das Chlorophyll. Die Adsorptionen, Berichte der Deutschen Chemischen Gesellschaf, Vol 24, No 6, page 316-323, 1906 (doi.org/10.1111/j.1438 8677.1906.tb06524.x)

  • M Tswett, Adsorptionsanalyse und chrematographische Methode. Anwendung auf die Chemie des Chlorophylls, Berichte der Deutschen Chemischen Gesellschaf, Vol 24, No 7, page 384-383, 1906. (doi:10.1111/j.1438-8677.1906.tb06534.x)

  • E Fischer, Synthese von Polypeptiden, Berichte der Deutschen Chemischen Gesellschaf, Vol 36, No 3, page 2982-2992, 1903. (doi/abs/10.1002/cber.19030360356)

  • P Gelmo, Über Sulfamide der p-Amidobenzolsulfonsäure, Journal für Praktische Chemie, Vol 77, No 1, page 369-382, 1907. (doi.org/10.1002/prac.19080770129)

  • Leo H. Baekeland, US Patent No. US942699A, 1909.

  • P Ehrlich, Experimental researches on specific therapy: on immunity with special relationship between distribution and action of antigens, Harben Lecture, London: Lewis, 1908.

  • O Diels and K Alder, Synthesen in der hydroaromatischen Reihe, Justus Liebigs Annalen der Chemie, Vol 460, No 1, page 98-122, 1928. (doi.org/10.1002/jlac.19284600106)

  • T Reichstein, A Grüssner and R Oppenauer, Synthesis of d- and l-Ascorbic Acid (Vitamin C), Nature, Vol 42, page 280, 1933. (doi.org/10.1038/132280b0)

  • D M Brown and A R Todd, Nucleotides. Part X. Some observations on the structure and chemical behaviour of the nucleic acids, J. Chem. Soc., page 5258, 1952. (doi.org/10.1039/JR9520000052)

  • A M Michelson and A R Todd, Nucleotides part XXXII. Synthesis of a dithymidine dinucleotide containing a 3′: 5′-internucleotidic linkage, J. Chem. Soc., page 2632-2638, 1955. (doi.org/10.1039/JR9550002632)

  • R Bonnett, J R Cannon, A W Johnson, I Sutherland, A Todd and E L Smith, Structure of Vitamin B12: The Structure of Vitamin B12 and its Hexacarboxylic Acid Degradation Product, Nature, Vol 176, page 328–330, 1955. (doi.org/10.1038/176328a0)

  • F Sanger and H Tuppy, The amino-acid sequence in the phenylalanyl chain of insulin. 1. The identification of lower peptides from partial hydrolysates, Biochemical Journal, Vol 49, No 4, page 463–481, 1951. (doi.org/10.1042/bj0490463)

  • S Anderson, M H L de Bruijn, A R Coulson, I C Eperon, F Sanger and G Young, Complete sequence of bovine mitochondrial DNA conserved features of the mammalian mitochondrial genome, Journal of Molecular Biology, Vol 156, No 4, page 683-717, 1982. (doi.org/10.1016/0022-2836(82)90137-1)

  • R B Woodward, W E Doering, The Total Synthesis Of Quinine1, J. Am. Chem. Soc., Vol 66, No 5, page 849, 1944. (doi.org/10.1021/ja01233a516)

  • V du Vigneaud, C Ressler, J M Swan, C W Roberts and P G Katsoyannis, The Synthesis of Oxytocin1, J. Am. Chem. Soc., Vol 76, No 12, page 3115– 3121, 1954. (doi.org/10.1021/ja01641a004)

  • R B Woodward, “A synthetic attack on the oestrone problem”, Thesis (Ph. D.), Massachusetts Institute of Technology, Department of Chemistry, 1937.

  • R B Woodward, F Sondheimer, D Taub, K Heusler and W M McLamore, The Total Synthesis of Steroids1, J. Am. Chem. Soc., Vol 74, No 17, page 4223– 4251, 1952. (doi.org/10.1021/ja01137a001)

  • R B Woodward, F E Bader, H Bickel, A J Frey and R W Kierstead, The Total Synthesis of Reserpine, J. Am. Chem. Soc., Vol 78, No 9, page 2023–2025, 1956.(doi.org/10.1021/ja01590a079)

  • Woodward et al., The Total Synthesis of Chlorophyll, J. Am. Chem. Soc., Vol 82, No 14, page 3800–3802, 1960.(doi.org/10.1021/ja01499a093)

  • Woodward et al., The Total Synthesis of Cephalosporin C1, J. Am. Chem. Soc., Vol 88, No 4, page 852–853, 1966.(doi.org/10.1021/ja00956a051)

  • R B Woodward, Recent advances in the chemistry of natural products, Pure Appl. Chem., Vol 25, No 1, page 283-304, 1971. (doi.org/10.1351/pac197125010283)

  • R B Woodward and R Hoffmann, Stereochemistry of Electrocyclic Reactions, J. Am. Chem. Soc., Vol 87, No 2, page 395–397, 1965. (doi.org/10.1021/ja01080a054)

  • E J Corey and X Min. Cheng, The Logic of Chemical Synthesis, John Wiley & Sons Ltd, Chichester, 1989.

  • G Wittig and U Schöllkopf, Über Triphenyl-phosphinmethylene als olefinbildende Reagenzien, Chemische Berichte., Vol 87, No 9, page 1318-1330, 1954. (doi.org/10.1002/cber.19540870919)

  • H C Brown and G Zweifel, Isomerization of Organoboranes Derived from Branched-Chain and Ring Olefins—Further Evidence for the EliminationAddition Mechanism of Isomerization, J. Am. Chem. Soc., Vol 82, No 6, page 1504–1505, 1960. (doi.org/10.1021/ja01491a058)

  • W S Johnson, M B Gravestock and B E McCarry, Acetylenic bond participation in biogenetic-like olefinic cyclizations. II. Synthesis of dl-progesterone, J. Am. Chem. Soc., Vol 93, No 17, page 4332–4334, 1971. (doi.org/10.1021/ja00746a062)

  • K C Nicolaou and E J Sorensen, Classics in total synthesis., Weinheim, Germany: VCH Publishers, 1996

  • Holton et al., First total synthesis of taxol. 1. Functionalization of the B ring, J. Am. Chem. Soc., Vol 116, No 4, page 1597–1598, 1994. (doi.org/10.1021/ja00083a066)

  • Danishefsky et al., Total Synthesis of Baccatin III and Taxol, J. Am. Chem. Soc., Vol 118, page 2843– 2859, 1996. (doi.org/10.1021/ja952692a)

  • Kuwajima et al., Enantioselective Total Synthesis of Taxol, J. Am. Chem. Soc., Vol 120, No 49, page 12980–12981, 1998. (doi.org/10.1021/ja9824932)

  • Wender et al., The Pinene Path to Taxanes. 6. A Concise Stereocontrolled Synthesis of Taxol, J. Am. Chem. Soc., Vol 119, No 11, page 2757–2758, 1997.(doi.org/10.1021/ja963539z)


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  • The History of Synthetic Organic Chemistry: A Journey from Urea to Taxol

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Authors

Biswajit Gayen
Department of Chemistry, Dr. Sudhir Chandra Sur Institute of Technology and Sports Complex, JIS Group of College, 540 Dum Dum, Kolkata-700074, India

Abstract


Synthetic Organic Chemistry is the backbone in modern Science. Nowadays, Organic Chemists are in such a triumph position that any complicated, bulky, stereo-chemically enriched and highly strained molecule can be synthesized very easily and within very short period of time. In 1828, German Chemist F. Wöhler first reported the synthesis of an Organic molecule namely, Urea from ammonium cyanate in his laboratory without any aid of microorganism. From that day, the journey of synthesis started. Then, Woodward introduced the method of how to synthesize targeted molecules by proper planning via retro-synthetic approach. Presently, Synthesis of Taxol (anti-cancer drug) can be achieved very smoothly in laboratory.

Keywords


History, synthetic, organic, chemistry, urea, taxol, natural products.

References





DOI: https://doi.org/10.24906/isc%2F2021%2Fv35%2Fi1%2F208409