Original scientific paper

In Search of Simplification: the Use of Topological Complexity Indices to Guide Retrosynthetic Analysis

Steven H. Bertz ; Complexity Study Center, Mendham, NJ 07945, USA
Christoph Rücker orcid.org/0000-0002-9287-3153 ; Department of Mathematics, University of Bayreuth, D-95440 Bayreuth, Germany

Abstract

Topological complexity indices N_S, N_T, N_S(lpe), N_T(lpe), twc and wcx are used to rank the one-bond disconnections of bicyclo[2.2.1]heptane, spiro[3.3]heptane and their aza derivatives with respect to the degree of simplification they afford. Selected two-bond disconnections of bicyclo[2.2.1]heptane and its aza derivatives are also evaluated. Simplification principles are derived which are useful for guiding the retrosynthetic analysis of complex target molecules. Comparison with the LHASA rules for strategic bonds reveals a great deal of similarity and some important differences.

Keywords

bicyclo[2.2.1]heptane; complexity indices; disconnections; retrosynthetic analysis; simplification principles; spiro
[3.3]heptane; strategic bonds; synthetic analysis; topological indices

Hrčak ID:

102667

URI

https://hrcak.srce.hr/102667

Publication date:

31.5.2004.

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