Molecular Acrobatics in Polycyclic Frames: Synthesis of “Kurmanediol” via Post-synthetic Modification of Cage Molecules by Olefinic Metathesis

We report late-stage ring-opening metathesis (ROM), ring-rearrangement metathesis (RRM), and ring-closing metathesis (RCM) approaches to generate expanded pentacycloundecane (PCUD) cage derivatives. These higher-order intricate polycyclic cage systems are aesthetically pleasing and structurally intr...

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Published in:Journal of organic chemistry 2023-08, Vol.88 (16), p.11650-11660
Main Authors: Kotha, Sambasivarao, Mehta, Gulazarahind
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Language:English
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creator Kotha, Sambasivarao
Mehta, Gulazarahind
description We report late-stage ring-opening metathesis (ROM), ring-rearrangement metathesis (RRM), and ring-closing metathesis (RCM) approaches to generate expanded pentacycloundecane (PCUD) cage derivatives. These higher-order intricate polycyclic cage systems are aesthetically pleasing and structurally intriguing. Their assembly maintains molecular symmetry during the entire synthetic sequence. To this end, metathesis-based catalysts are used to execute the ROM, RRM, and RCM strategies. The synthetic approach to these cage polycycles involves the Diels–Alder reaction, [2 + 2] photocycloaddition, RRM, ROM, and RCM as key steps.
doi_str_mv 10.1021/acs.joc.3c00968
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title Molecular Acrobatics in Polycyclic Frames: Synthesis of “Kurmanediol” via Post-synthetic Modification of Cage Molecules by Olefinic Metathesis
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