Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 47, Pages 12107-12120Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201705919
Keywords
carbocycles; cyclization; fragmentation; nine-membered ring; ring-expansion
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Funding
- Funds of the European Research Council under the European Union's Horizon 2020 research and innovation program [714049]
- Chemical Industry (Sachkostenzuschuss)
- German Research Foundation (Emmy Noether Fellowship) [SFB 749, SFB TRR 152]
- German National Academic Foundation
- Chemical Industry (Dozentenpreis)
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Many natural products comprising a nine-membered carbocyclic core structure exhibit interesting biological effects. However, only a minority have succumbed to their synthesis in the past. The synthesis of functionalized nine-membered carbocycles still remains a challenging goal for synthetic chemists, mainly due to their high ring strain. Different strategies to overcome the unfavorable enthalpic and entropic factors associated with their formation are highlighted in this Concept article. The presented methods are classified into two different categories: (1) the ring-expansion of smaller rings or the ring-contraction of larger rings and (2) the direct cyclization of acyclic precursors.
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