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Volumn 77, Issue 1-2, 2004, Pages 221-235

In search of simplification: The use of topological complexity indices to guide retrosynthetic analysis

Author keywords

Bicyclo 2.2.1 heptane; Complexity indices; Disconnections; Retrosynthetic analysis; Simplification principles; Spiro 3.3 heptane; Strategic bonds; Synthetic analysis; Topological indices

Indexed keywords

HETEROCYCLIC COMPOUND; NORBORNANE DERIVATIVE;

EID: 3042780580     PISSN: 00111643     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (5)

References (85)
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    • For part 22, see Ref. 29a. For part 21, see Ref. 29b
    • For part 22, see Ref. 29a. For part 21, see Ref. 29b.
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    • See also Ref. 21
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    • see also Ref. 11
    • (d) see also Ref. 11.
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    • J. Devillers and A. T. Balaban (Eds.), Gordon and Breach, Reading, UK
    • (b) D. Bonchev, in: J. Devillers and A. T. Balaban (Eds.), Topological Indices and Related Descriptors, Gordon and Breach, Reading, UK, 1999, pp. 361-401;
    • (1999) Topological Indices and Related Descriptors , pp. 361-401
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    • see also Refs. 3c, 5c and 9b
    • (e) see also Refs. 3c, 5c and 9b.
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    • T. H. Pierce and B. A. Hohne (Eds.), ACS Symp. Ser., Am. Chem. Soc., Washington, DC
    • (e) S. H. Bertz and W. C. Herndon, in: T. H. Pierce and B. A. Hohne (Eds.), Artificial Intelligence Applications in Chemistry, ACS Symp. Ser., Vol. 306, Am. Chem. Soc., Washington, DC, 1986, pp. 169-175;
    • (1986) Artificial Intelligence Applications in Chemistry , vol.306 , pp. 169-175
    • Bertz, S.H.1    Herndon, W.C.2
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    • see also Ref. 3a
    • (g) see also Ref. 3a.
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  • 45
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    • see also Ref. 10c
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    • see also Refs. 7a-d
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  • 59
    • 0034693180 scopus 로고    scopus 로고
    • intramolecular
    • for other Diels-Alder approaches, see (b) T. K. M. Shing and Q. Jiang, J. Org. Chem. 65 (2000) 7059-7069 (intramolecular); (c) N. Stojanac and Z. Valenta, Can. J. Chem. 69 (1991) 853-855; (d) G. Vidari, S. Ferriño, and P. A. Grieco, J. Am. Chem. Soc. 106 (1984), 3539-3548 (first total synthesis).
    • (2000) J. Org. Chem. , vol.65 , pp. 7059-7069
    • Shing, T.K.M.1    Jiang, Q.2
  • 60
    • 0034693180 scopus 로고    scopus 로고
    • for other Diels-Alder approaches, see (b) T. K. M. Shing and Q. Jiang, J. Org. Chem. 65 (2000) 7059-7069 (intramolecular); (c) N. Stojanac and Z. Valenta, Can. J. Chem. 69 (1991) 853-855; (d) G. Vidari, S. Ferriño, and P. A. Grieco, J. Am. Chem. Soc. 106 (1984), 3539-3548 (first total synthesis).
    • (1991) Can. J. Chem. , vol.69 , pp. 853-855
    • Stojanac, N.1    Valenta, Z.2
  • 61
    • 0000692999 scopus 로고
    • first total synthesis
    • for other Diels-Alder approaches, see (b) T. K. M. Shing and Q. Jiang, J. Org. Chem. 65 (2000) 7059-7069 (intramolecular); (c) N. Stojanac and Z. Valenta, Can. J. Chem. 69 (1991) 853-855; (d) G. Vidari, S. Ferriño, and P. A. Grieco, J. Am. Chem. Soc. 106 (1984), 3539-3548 (first total synthesis).
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3539-3548
    • Vidari, G.1    Ferriño, S.2    Grieco, P.A.3
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    • 3042748710 scopus 로고    scopus 로고
    • note
    • Sometimes, bonds must be formed in the retrosynthetic direction for strategic reasons, e.g., the retro-Diels-Alder reaction has been used synthetically, and its transform is the Diels-Alder reaction, which has a relatively large positive value of ΔC. See also Ref. 12a.
  • 72
    • 3042796397 scopus 로고    scopus 로고
    • note
    • An analogy is cities, represented by points on a map, and the roads that connect them, represented by lines. When there is one road to a city, there is no choice of routes; however, when there are two roads, a decision must be made as to which route to take, making the problem more complex. The number of choices increases factorially as roads are added.
  • 75
    • 3042836886 scopus 로고    scopus 로고
    • note
    • Originally, a factor of 1/2 was included in the formula for two to compensate for the fact that each walk is counted twice without it (Refs. 8a, c). It was later dropped for other reasons (Refs. 3a and 8b).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.