''A way of thinking backwards'': Computing and method in synthetic organic chemistry

Historical Studies in the Natural Sciences

Volumn 48, Issue 3, 2018, Pages 300-337

  Hepler Smith, Evan ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Artificial intelligence; Computing; E. J. Corey; LHASA; Method; Organic chemistry; Pedagogy; Synthesis

Indexed keywords

EID: 85053717506     PISSN: 19391811     EISSN: 1939182X     Source Type: Journal    
DOI: 10.1525/hsns.2018.48.3.300     Document Type: Article

References (71)

1. Stuart Warren and Paul Wyatt, Organic Synthesis: The Disconnection Approach, 2nd ed. (West Sussex, UK: Wiley, 2008), 1.
2. Roald Hoffmann, ''Why Think Up New Molecules, '' in Roald Hoffmann on the Philosophy, Art, and Science of Chemistry, ed. Jeffrey Kovac and Michael Weisberg (New York: Oxford University Press, 2012), 114-19, on 114.
3. American Chemistry Council, 2016 Guide to the Business of Chemistry (Arlington, VA: American Chemistry Council, 2016), 37.
4. K. C. Nicolaou et al., ''The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century, '' ANIE 39, no. 1 (2000): 44-122, on 45.
5. William R. Newman and Bernadette Bensaude-Vincent, The Artificial and the Natural: An Evolving Polarity (Cambridge, MA: MIT Press, 2007)
6. Sophia Roosth, Synthetic: How Life Got Made (Chicago: University of Chicago Press, 2017).
7. Alan J. Rocke, Nationalizing Science: Adolphe Wurtz and the Battle for French Chemistry (Cambridge, MA: MIT Press, 2001), 248.
8. K. C. Nicolaou, E. J. Sorensen, and N. Winssinger, ''The Art and Science of Organic and Natural Products Synthesis, '' JCE 75, no. 10 (1998): 1225-58, on 1232.
9. P. J. Stang, ''124 Years of Publishing Original and Primary Chemical Research, '' JACS 125, no. 1 (2003): 1-8, on 1.
10. Peter J. T. Morris, ''The Fall and Rise of the History of Recent Chemistry, '' Ambix 58, no. 3 (2011): 238-56.
11. Anthony Cook et al., ''Computer-Aided Synthesis Design: 40 Years On, '' Wiley Interdisciplinary Reviews: Computational Molecular Science 2, no. 1 (2012): 79-107, on 81.
12. Sara Szymkucét al., ''Computer- Assisted Synthetic Planning: The End of the Beginning, '' ANIE 55, no. 20 (2016): 5904-37.
13. Phillip Judson, Knowledge-Based Expert Systems in Chemistry: Not Counting on Computers (Cambridge: Royal Society of Chemistry, 2009), 31.
14. Carsten Reinhardt, Shifting and Rearranging: Physical Methods and the Transformation of Modern Chemistry (Sagamore Beach, MA: Science History Publications/USA, 2006).
15. Lorraine J. Daston, ''The Physicalist Tradition in Early Nineteenth Century French Geometry, '' Studies in History and Philosophy of Science Part A 17, no. 3 (1986): 269-95
16. Matthew L. Jones, Reckoning with Matter: Calculating Machines, Innovation, and Thinking about Thinking from Pascal to Babbage (Chicago: University of Chicago Press, 2016).
17. Jon Agar, ''What Difference Did Computers Make?, '' Social Studies of Science 36, no. 6 (2006): 869-907, on 898-900.
18. David Sepkoski, ''The Database before the Computer?, '' Osiris 32, no. 1 (2017): 175-201.
19. Hallam Stevens, Life Out of Sequence: A Data-Driven History of Bioinformatics (Chicago: University of Chicago Press, 2013), 5
20. Hallam Stevens, ''A Feeling for the Algorithm: Working Knowledge and Big Data in Biology, '' Osiris 32, no. 1 (2017): 151-74.
21. Stephanie Dick, ''AfterMath: The Work of Proof in the Age of Human-Machine Collaboration, '' Isis 102, no. 3 (2011): 494-505
22. Stephanie Dick, ''Of Models and Machines: Implementing Bounded Rationality, '' Isis 106, no. 3 (2015): 623-34.
23. John Hedley Brooke, ''Organic Synthesis and the Unification of Chemistry-A Reappraisal, '' The British Journal for the History of Science 5, no. 4 (1971): 363-92, on 375.
24. C. A. Russell, ''The Changing Role of Synthesis in Organic Chemistry, '' Ambix 34, no. 3 (1987): 169-80.
25. Ursula Klein, Experiments, Models, Paper Tools: Cultures of Organic Chemistry in the Nineteenth Century (Stanford, CA: Stanford University Press, 2003).
26. Catherine M. Jackson, ''Chemical Identity Crisis: Glass and Glassblowing in the Identification of Organic Compounds, '' Annals of Science 72, no. 2 (2015): 187-205.
27. Catherine M. Jackson, ''Synthetical Experiments and Alkaloid Analogues: Liebig, Hofmann and the Origins of Organic Synthesis, '' Historical Studies in the Natural Sciences 44, no. 4 (2014): 319-63.
28. Jeffrey I. Seeman, ''On the Relationship between Classical Structure Determination and Retrosynthetic Analysis/ Total Synthesis, '' Israel Journal of Chemistry 57, no. 1-2 (2018): 28-44.
29. Leo B. Slater, ''Woodward, Robinson, and Strychnine: Chemical Structure and Chemists' Challenge, '' Ambix 48, no. 3 (2001): 161-89.
30. Andre Siegel, ''Sir Robert Robinson's 'Anthocyanin Period': 1922-1934-A Case Study of an Early Twentieth-Century Natural Products Synthesis, '' Ambix 55, no. 1 (2008): 62-82.
31. Peter Morris, ed., From Classical to Modern Chemistry: The Instrumental Revolution (Cambridge: Royal Society of Chemistry, 2002).
32. Kostas Gavroglu and Ana Simões, Neither Physics nor Chemistry: A History of Quantum Chemistry (Cambridge, MA: MIT Press, 2012).
33. Mary Jo Nye, From Chemical Philosophy to Theoretical Chemistry: Dynamics of Matter and Dynamics of Disciplines, 1800-1950 (Berkeley: University of California Press, 1993), 196-223;
34. Albert Eschenmoser and Claude E. Wintner, ''Natural Product Synthesis and Vitamin B12, '' Science 196, no. 4297 (1977): 1410-20, on 1410-13.
35. Alexander Todd and John Cornforth, ''Robert Burns Woodward, '' Biographical Memoirs of Fellows of the Royal Society 27 (1981): 628-95, on 641.
36. R. B. Woodward, ''Synthesis, '' in Perspectives in Organic Chemistry, ed. Alexander R. Todd (New York: Interscience, 1956), 155-84, on 158.
37. R. B. Woodward et al., ''The Total Synthesis of Strychnine, '' Tetrahedron 19, no. 2 (1963): 247-88, on 248.
38. R. B. Woodward, ''The Total Synthesis of Chlorophyll, '' Pure and Applied Chemistry 2, no. 3-4 (1961): 383-404, on 383;
39. R. B. Woodward, ''Art and Science in the Synthesis of Organic Compounds: Retrospect and Prospect, '' in Pointers and Pathways in Research: Six Lectures in the Fields of Organic Chemistry and Medicine, ed. Maeve O'Connor (Bombay: CIBA of India Ltd., 1963), 22-41, on 41.
40. Charles R. Allerson, ''Elias J. Corey, '' in Nobel Laureates in Chemistry, 1901-1992 (Washington, DC: American Chemical Society, 1993), 750-58
41. A. Maureen Rouhi, ''Above and Beyond Organic Synthesis, '' C&EN 82, no. 13 (2004): 37-41
42. E. J. Corey, ''Impossible Dreams, '' Journal of Organic Chemistry 69, no. 9 (2004): 2917-19.
43. E. J. Corey, interview by author, Cambridge, MA, 6 Aug 2013 (recording in author's possession).
44. Romeo B. Wagner and Harry D. Zook, Synthetic Organic Chemistry (New York: Wiley, 1953);
45. Vartkes Migrdichian, Organic Synthesis (New York: Reinhold, 1957).
46. David Kaiser, ed., Pedagogy and the Practice of Science: Historical and Contemporary Perspectives (Cambridge, MA: MIT Press, 2005).
47. Michael D. Gordin, A Well-Ordered Thing: Dmitrii Mendeleev and the Shadow of the Periodic Table (New York: Basic Books, 2004), 15-45.
48. E. J. Corey, ''General Methods for the Construction of Complex Molecules, '' Pure and Applied Chemistry 14, no. 1 (1967): 19-38.
49. E. J. Corey and W. Todd Wipke, ''Computer-Assisted Design of Complex Organic Syntheses, '' Science 166, no. 3902 (1969): 178-92.
50. Robert K. Lindsay, Applications of Artificial Intelligence for Organic Chemistry: The DENDRAL Project (New York: McGraw-Hill, 1980);
51. Joseph Adam November, Biomedical Computing: Digitizing Life in the United States (Baltimore: Johns Hopkins University Press, 2012), 237-68.
52. E. J. Corey, ''Computer-Assisted Analysis of Complex Synthetic Problems, '' Quarterly Review of the Chemical Society 25, no. 4 (1971): 455-82, on 456n1.
53. Robert E. Ireland, Organic Synthesis (Englewood Cliffs, NJ: Prentice-Hall, 1969), 17.
54. E. J. Corey et al., ''Computer-Assisted Synthetic Analysis. Long-Range Search Procedures for Antithetic Simplification of Complex Targets by Application of the Halolactonization Transform, '' Journal of Chemical Information and Computer Sciences 20, no. 4 (1980): 221-30, on 226.
55. Rebecca M. Wilson and Samuel J. Danishefsky, ''Pattern Recognition in Retrosynthetic Analysis: Snapshots in Total Synthesis, '' Journal of Organic Chemistry 72, no. 12 (2007): 4293-4305.
56. W. Clark Still, ''Synthesis Sheets: An Aid to Synthetic Analysis, '' JCE 50, no. 6 (1973): 378-79.
57. Martin D. Burke and Gojko Lalic, ''Teaching Target-Oriented and Diversity-Oriented Organic Synthesis at Harvard University, '' Chemistry & Biology 9, no. 5 (2002): 535-41, on 535-36;
58. H. W. Orf, ''Computer-Assisted Instruction in Organic Synthesis, '' JCE 52, no. 7 (1975):
59. Robert D. Stolow and Leo J. Joncas, ''Computer-Assisted Teaching of Organic Synthesis, '' JCE 57, no. 12 (1980): 868-73.
60. Stephen Turner, The Design of Organic Syntheses (New York: Elsevier, 1976), 9.
61. Stephen Turner, An Introduction to the Design of Organic Synthesis (England: Koch-Light Laboratories Ltd., 1971), 9.
62. Stuart G. Warren, Organic Synthesis: The Disconnection Approach, 1st ed. (New York: Wiley, 1982).
63. Stuart G. Warren, Designing Organic Syntheses: A Programmed Introduction to the Synthon Approach (New York: Wiley, 1978).
64. Patrick T. Flaherty, ''Book Review of Organic Synthesis: The Disconnection Approach. Second Edition, '' Journal of Medicinal Chemistry 52, no. 18 (2009): 5768-69.
65. Eric N. Jacobsen and David W. C. MacMillan, ''Organocatalysis, '' Proceedings of the National Academy of Sciences 107, no. 48 (2010): 20618-19.
66. W. D. Ihlenfeldt and J. Gasteiger, ''Computer-Assisted Planning of Organic Syntheses: The Second Generation of Programs, '' ANIE 34, no. 23-24 (1995): 2613-33, on 2613.
67. David Kaiser, Drawing Theories Apart: The Dispersion of Feynman Diagrams in Postwar Physics (Chicago: University of Chicago Press, 2005).
68. R. B. Woodward, ''An Account of Professor Elias J. Corey's Contributions to Chemistry'' (Medal of Science Nomination), n.d. [1976], RBW Papers, Box 4, Folder ''Corey [1976-78].''
69. Jeannette M. Wing, ''Computational Thinking, '' Communications of the ACM 49, no. 3 (2006): 33-35.
70. Jonathan D. Culler, Structuralist Poetics: Structuralism, Linguistics, and the Study of Literature (Ithaca, NY: Cornell University Press, 1975), 76, 258-59;
71. Thomas S. Kuhn, ''Second Thoughts on Paradigms, '' in The Essential Tension: Selected Studies in Scientific Tradition and Change (Chicago: University of Chicago Press, 1977), 293-319.