Phytochemistry Reviews

, Volume 12, Issue 4, pp 603–651 | Cite as

Synthetic approaches to polycyclic semiochemicals and their derivatives: combinatorial methods towards phytochemicals



Semiochemicals are natural products occurring in plants, bacteria or animals which function as carriers of a special message. Depending on the mode of function of the semiochemicals, they are divided into pheromones that trigger a response in members of the same species and allelochemicals (kairomones, allomones) that act between individuals of different species. Semiochemicals are very important compounds that influence the behavior of plants and animals and their adaption to a changing environment. As their importance for plants, animals and the ecological system itself is huge, the synthetic access to these chemicals, their precursors and derivatives is of high interest. Beyond novel strategies for the construction of semiochemical skeletons, combinatorial methods have been implemented to synthesize medium-sized and large-sized libraries that enable diverse modifications of the active compounds. These combinatorial approaches allow the screening for more active compounds and they elucidate the mode of action of the semiochemical or of the biological target. This review summarizes the state of the art procedures for the synthesis of important skeletons appearing in semiochemicals and gives special synthetic procedures for selected examples if the procedure is suitable for a general transfer to the synthesis of derivatives. The synthetic examples are given in the context of known active phytochemicals and their function that allows an evaluation of the given procedures with respect to the fulfillment of the common structural requirements (the structural diversity and flexibility) and the importance for the regulation of biological systems. Parts of this review were given in a lecture at the BioCom 12 in Cadiz, 2012.


Combinatorial synthesis Indole alkaloids Natural products Oxygen heterocycles Solid-phase synthesis 





n-Butyl lithium




Cannabinoid receptor 1


Cannabinoid receptor 2


Cyclic adenosine monophosphate






Hypersensitive acid-labile


6-Benzyl aminopurine


Di-tert-butyl dicarbonate










Dimethyl acetylenedicarboxylate














Desoxyribonucleic acid


Domino oxa-Michael-aldol












Lithium diisopropylamide


Lithium bis(trimethylsilyl)amide


Meta-chloroperoxybenzoic acid




Microwave irradiation






Protecting group




Nucleophilic aromatic substitution






Trifluoroacetic acid




Tetrapropylammonium perruthenate


Tumor necrosis factor (TNF)-related apoptosis-inducing ligand


Transfer ribonucleic acid


Room temperature


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Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Nicole Jung
    • 1
    • 2
  • Franziska Gläser
    • 1
  • Stefan Bräse
    • 1
    • 2
  1. 1.Institute of Organic ChemistryKarlsruhe Institute of Technology (KIT)KarlsruheGermany
  2. 2.Institute of Toxicology and GeneticsKarlsruhe Institute of Technology (KIT)Eggenstein-LeopoldshafenGermany

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