Streamlined synthesis of functionalized dibenzo[a,e]pentalenes through potassium-mediated cyclization and late-stage thianthrenation

Marcell M. Bogner; Bence Sóvári; Péter P. Kalapos; Péter J. Mayer; Márton Hegedűs; Gábor Turczel; Anna J. Kiss-Szemán; Veronika Harmat; Attila Kunfi; Gábor London

doi:10.1039/D6RA03886G

Streamlined synthesis of functionalized dibenzo[a,e]pentalenes through potassium-mediated cyclization and late-stage thianthrenation

Marcell M. Bogner,

^a Bence Sóvári,

^a Péter P. Kalapos,^a Péter J. Mayer,

^a Márton Hegedűs,^a Gábor Turczel,

^b Anna J. Kiss-Szemán,

^c Veronika Harmat,^cd Attila Kunfi

^a and Gábor London

*^a

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, 1117 Budapest, Hungary
E-mail: london.gabor@ttk.hu

^b Centre for Structural Science, HUN-REN Research Centre for Natural Sciences, 1117 Budapest, Hungary

^c Laboratory of Structural Chemistry and Biology, Institute of Chemistry, Eötvös Loránd University, Pázmány Péter sétány 1/A, Budapest, Hungary

^d HUN-REN ELTE Protein Modelling Research Group, Pázmány Péter sétány 1/A, Budapest, Hungary

Abstract

Herein we report a simple and scalable synthetic platform for the dibenzo[a,e]pentalene (DBP) framework. Via potassium-mediated cyclization of TIPS-protected phenylacetylene we were able to produce multi-decagram-scale (>25 g) quantities of a 5,10-TIPS protected DBP key intermediate, which enabled further complexity-enhancing transformations. Halodesilylations on the pentalene core and aryl thianthrenation on the annulated benzene rings enabled highly modular synthetic pathways towards complex DBP-based structures.

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Streamlined synthesis of functionalized dibenzo[a,e]pentalenes through potassium-mediated cyclization and late-stage thianthrenation

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Streamlined synthesis of functionalized dibenzo[a,e]pentalenes through potassium-mediated cyclization and late-stage thianthrenation

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