Optimization in organic synthesis

Medicinal Research Reviews

Volumn 19, Issue 5, 1999, Pages 342-347

  Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BIOTRANSFORMATION; CATALYSIS; COMPUTER AIDED DESIGN; CONFERENCE PAPER; COST EFFECTIVENESS ANALYSIS; ORGANIC CHEMISTRY; SYNTHESIS; TECHNOLOGY;

CHEMICAL ENGINEERING; CHEMISTRY, ORGANIC; DRUG DESIGN; HUMANS; ORGANIC CHEMICALS;

EID: 0032859722     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1128(199909)19:5<342::AID-MED2>3.0.CO;2-E     Document Type: Conference Paper

References (93)

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37. Selective cross-coupling reactions between C(sp3) and C(sp2) centers had been one of the most difficult tasks in carbon-carbon bond synthesis until the early 1970s. . . Now, . . .(it) has become the reaction of first choice for this purpose. Tamao K. Comprehensive organic synthesis. London: Pergamon Press; Vol 3, 1991. p 435.
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48. "Anyone who has helped to plan an industrial synthesis tends to pity the poverty of the criteria that academic synthesis must meet. Work of this sort ought to be held in greater respect and published more often than, alas, it is." See ref 5e.
49. "The more innocuous the process change appears, the further its influence will extend." I am grateful to Trevor Laird, Scientific Update, for this Process Chemist's credo.
50. Avoided common usage by persuasion from Sir John Cornforth, see Ref 5(e).
51. The ideal synthesis produces the target molecule in one step and 100% yield from readily available materials through a process that is safe, efficient, and environmentally sound. Wender PA. cited in Zurer PS. C & EN, May 5, 1997, p 47.
52. For a comment on this issue, see Ref 5(b), footnote 11.
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59. Hendrickson JB. Angew Chem Int Ed Engl 1990;29:1286; Hendrickson JB. J Am Chem Soc 1991;113:902 and refs cited therein; Gasteiger J, Gillespie PD, Marquarding D, Hanessian S, Franco J, Larouche B. Pure Appl Chem 1990;62:1887; Hanessian S, Franco J, Gagnon G, Laramee D, Larouche BJ. Chem Inf Comput Sci 1990;30:413; Helson HE, Jorgensen WL. J Org Chem 1994;59:3841; Ugi I. Top Curr Chem 1974; 48:1.
60. Hendrickson JB. Angew Chem Int Ed Engl 1990;29:1286; Hendrickson JB. J Am Chem Soc 1991;113:902 and refs cited therein; Gasteiger J, Gillespie PD, Marquarding D, Hanessian S, Franco J, Larouche B. Pure Appl Chem 1990;62:1887; Hanessian S, Franco J, Gagnon G, Laramee D, Larouche BJ. Chem Inf Comput Sci 1990;30:413; Helson HE, Jorgensen WL. J Org Chem 1994;59:3841; Ugi I. Top Curr Chem 1974; 48:1.
61. Hendrickson JB. Angew Chem Int Ed Engl 1990;29:1286; Hendrickson JB. J Am Chem Soc 1991;113:902 and refs cited therein; Gasteiger J, Gillespie PD, Marquarding D, Hanessian S, Franco J, Larouche B. Pure Appl Chem 1990;62:1887; Hanessian S, Franco J, Gagnon G, Laramee D, Larouche BJ. Chem Inf Comput Sci 1990;30:413; Helson HE, Jorgensen WL. J Org Chem 1994;59:3841; Ugi I. Top Curr Chem 1974; 48:1.
62. Hendrickson JB. Angew Chem Int Ed Engl 1990;29:1286; Hendrickson JB. J Am Chem Soc 1991;113:902 and refs cited therein; Gasteiger J, Gillespie PD, Marquarding D, Hanessian S, Franco J, Larouche B. Pure Appl Chem 1990;62:1887; Hanessian S, Franco J, Gagnon G, Laramee D, Larouche BJ. Chem Inf Comput Sci 1990;30:413; Helson HE, Jorgensen WL. J Org Chem 1994;59:3841; Ugi I. Top Curr Chem 1974; 48:1.
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64. Bertz SH, Sommer TJ. In: Hudlicky T, editor. Organic synthesis: Theory and applications. Greenwich, CT: JAI Press; 1993. Vol. 2, p. 67; Wender PA, Miller BL. ibid 1993. Vol. 2, p 27.
65. Whitlock HW. J Org Chem 1998;63:7982; Chanon M, Barone R, Baralotto C, Julliard M, Hendrickson JB. Synthesis 1998;1559. In the latter review, a fascinating mountain metaphor for synthetic strategy is described and illustrated.
66. Whitlock HW. J Org Chem 1998;63:7982; Chanon M, Barone R, Baralotto C, Julliard M, Hendrickson JB. Synthesis 1998;1559. In the latter review, a fascinating mountain metaphor for synthetic strategy is described and illustrated.
67. An efficiency factor of step:person may be an interesting analysis.
68. Stated in various ways by many synthetic chemists, most recently by Gilbert Stork: The important question is, after the work is done, what do you know that you didn't before? Cope Symposium Lecture, ACS Meeting, Anaheim, CA, March, 1999 (C & EN, April 5, 1999, p 33).
69. Stated in various ways by many synthetic chemists, most recently by Gilbert Stork: The important question is, after the work is done, what do you know that you didn't before? Cope Symposium Lecture, ACS Meeting, Anaheim, CA, March, 1999 (C & EN, April 5, 1999, p 33).
70. . . . . other things being equal, that field has the most merit which contributes most heavily to, and illuminates most brightly, its neighbouring scientific disciplines. Weinberg AM. Minerva, 1963;2:159. Biological chemistry: Hinterding K, Alonso-Diaz D, Waldmann H. Angew Chem Int Ed Engl 1998;37:689; material science: Dagani R. C & EN June 8, 1998 p 35; Rouh AM. ibid April 20, 1998, p 57.
71. . . . . other things being equal, that field has the most merit which contributes most heavily to, and illuminates most brightly, its neighbouring scientific disciplines. Weinberg AM. Minerva, 1963;2:159. Biological chemistry: Hinterding K, Alonso-Diaz D, Waldmann H. Angew Chem Int Ed Engl 1998;37:689; material science: Dagani R. C & EN June 8, 1998 p 35; Rouh AM. ibid April 20, 1998, p 57.
72. . . . . other things being equal, that field has the most merit which contributes most heavily to, and illuminates most brightly, its neighbouring scientific disciplines. Weinberg AM. Minerva, 1963;2:159. Biological chemistry: Hinterding K, Alonso-Diaz D, Waldmann H. Angew Chem Int Ed Engl 1998;37:689; material science: Dagani R. C & EN June 8, 1998 p 35; Rouh AM. ibid April 20, 1998, p 57.
73. . . . . other things being equal, that field has the most merit which contributes most heavily to, and illuminates most brightly, its neighbouring scientific disciplines. Weinberg AM. Minerva, 1963;2:159. Biological chemistry: Hinterding K, Alonso-Diaz D, Waldmann H. Angew Chem Int Ed Engl 1998;37:689; material science: Dagani R. C & EN June 8, 1998 p 35; Rouh AM. ibid April 20, 1998, p 57.
74. Most if not all of the known types of organic derivatives of silicon have been considered. . . the prospect of any immediate and important advances in this section of organic chemistry does not seem to be very hopeful. Kipping FS. Proc Royal Soc A 1937;159:139.
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76. Reviews: Mikami K, Korenaga T, Matsukawa S, Matsumoto Y, Ding K, Ishii A, Volk T, Terada MJ. Syn Org Chem Jpn 1998;56:975; Noyori R, Kitamura M. Angew Chem Int Ed Engl 1991;30:49; Kagan HB, Guillaneux D, Rainford D, Samuel O, Zhao S-H. Acta Chem Scand 1996;50:345; Avalos M, Babiano R, Cintas P, Jimenez JL. Palacios JC. Tetrahedron Asymm 1997;8:2997.
77. Reviews: Mikami K, Korenaga T, Matsukawa S, Matsumoto Y, Ding K, Ishii A, Volk T, Terada MJ. Syn Org Chem Jpn 1998;56:975; Noyori R, Kitamura M. Angew Chem Int Ed Engl 1991;30:49; Kagan HB, Guillaneux D, Rainford D, Samuel O, Zhao S-H. Acta Chem Scand 1996;50:345; Avalos M, Babiano R, Cintas P, Jimenez JL. Palacios JC. Tetrahedron Asymm 1997;8:2997.
78. Reviews: Mikami K, Korenaga T, Matsukawa S, Matsumoto Y, Ding K, Ishii A, Volk T, Terada MJ. Syn Org Chem Jpn 1998;56:975; Noyori R, Kitamura M. Angew Chem Int Ed Engl 1991;30:49; Kagan HB, Guillaneux D, Rainford D, Samuel O, Zhao S-H. Acta Chem Scand 1996;50:345; Avalos M, Babiano R, Cintas P, Jimenez JL. Palacios JC. Tetrahedron Asymm 1997;8:2997.
79. McCoy M. C & EN, January 4, 1999, p 10. For the development of enantioselective mutants for biocatalysis, see Reetz MT, Zonta A, Schimossek K, Liebeton K, Jaeger K-E. Angew Chem Int Ed Engl 1997;36: 2830. For facilitation of availability of valuable natural products by recombinant microbial biocatalysis, see Draths KM, Knop DR, Frost JW. J Am Chem Soc 1999;121:1603.
80. McCoy M. C & EN, January 4, 1999, p 10. For the development of enantioselective mutants for biocatalysis, see Reetz MT, Zonta A, Schimossek K, Liebeton K, Jaeger K-E. Angew Chem Int Ed Engl 1997;36: 2830. For facilitation of availability of valuable natural products by recombinant microbial biocatalysis, see Draths KM, Knop DR, Frost JW. J Am Chem Soc 1999;121:1603.
81. McCoy M. C & EN, January 4, 1999, p 10. For the development of enantioselective mutants for biocatalysis, see Reetz MT, Zonta A, Schimossek K, Liebeton K, Jaeger K-E. Angew Chem Int Ed Engl 1997;36: 2830. For facilitation of availability of valuable natural products by recombinant microbial biocatalysis, see Draths KM, Knop DR, Frost JW. J Am Chem Soc 1999;121:1603.
82. Kobayashi S, Nagayama S. J Am Chem Soc 1998;120:2985; Kobayashi S, Nagayama S, Busujima T. ibid 1998;120:8287.
83. Kobayashi S, Nagayama S. J Am Chem Soc 1998;120:2985; Kobayashi S, Nagayama S, Busujima T. ibid 1998;120:8287.
84. Borman S. C & EN March 8, 1999, p 33.
85. Guiles JW, Lanter CL, Rivero RA. Angew Chem Int Ed Engl 1998;37:926.
86. See Shaughnessy KH, Kim P, Hartwig JF. J Am Chem Soc 1999;121:2123 for an excellent list of citations.
87. For an opinion, see Sharpless KB. cited in C & EN, April 15, 1999, p 33.
88. For insightful views on process R & D, see Laird T. Org Process Res Dev 1997;1:95, 257.
89. McCan M. C & EN July 27, 1998; Stinson SC. C & EN July 13, 1998.
90. McCan M. C & EN July 27, 1998; Stinson SC. C & EN July 13, 1998.
91. Previous symposia: 81 st Canadian Society for Chemistry (CSC) Meeting, May 31-June 1, 1998, Whistler, BC Canada: 213th ACS Meeting, April 14-16, 1997, San Francisco. Future symposium: 83rd CSC Meeting, Calgary, Alberta, June, 2000.
92. Previous symposia: 81 st Canadian Society for Chemistry (CSC) Meeting, May 31-June 1, 1998, Whistler, BC Canada: 213th ACS Meeting, April 14-16, 1997, San Francisco. Future symposium: 83rd CSC Meeting, Calgary, Alberta, June, 2000.
93. Previous symposia: 81 st Canadian Society for Chemistry (CSC) Meeting, May 31-June 1, 1998, Whistler, BC Canada: 213th ACS Meeting, April 14-16, 1997, San Francisco. Future symposium: 83rd CSC Meeting, Calgary, Alberta, June, 2000.