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Issue 27, 2018, Issue in Progress
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Synthesis of propellanes containing a bicyclo[2.2.2]octene unit via the Diels–Alder reaction and ring-closing metathesis as key steps

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Abstract

The synthesis of propellanes containing bicyclo[2.2.2]octene via olefin metathesis approach is less explored. Herein, we describe a simple and convenient method to synthesize propellane derivatives containing a bicyclo[2.2.2]octene unit which are structurally similar to 11β-HSD1 inhibitors by sequential usage of the Diels–Alder reaction, C-allylation and ring-closing metathesis (RCM) as the key steps. Additionally, we expanded this approach to an endo-tricyclo[4.2.2.02,5]decene derivative which is a useful monomer for polymer synthesis and we have also synthesized basketene and anthracene-based propellanes using the same strategy.

Graphical abstract: Synthesis of propellanes containing a bicyclo[2.2.2]octene unit via the Diels–Alder reaction and ring-closing metathesis as key steps

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Publication details

The article was received on 28 Mar 2018, accepted on 03 Apr 2018 and first published on 19 Apr 2018


Article type: Paper
DOI: 10.1039/C8RA02687D
Citation: RSC Adv., 2018,8, 14906-14915
  • Open access: Creative Commons BY-NC license
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    Synthesis of propellanes containing a bicyclo[2.2.2]octene unit via the Diels–Alder reaction and ring-closing metathesis as key steps

    S. Kotha and S. Pulletikurti, RSC Adv., 2018, 8, 14906
    DOI: 10.1039/C8RA02687D

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