Total synthesis of polymorphatin A, a macrocyclic bisbibenzyl with boat configured arenes
Total synthesis of polymorphatin A, a macrocyclic bisbibenzyl with boat configured arenes
Polymorphatin A was reported as a constituent of Marchantia polymorpha in 2007 following much speculation as to its likely existence as a natural product. Interest was rekindled when a claimed total synthesis revealed inconsistencies in spectral data between the synthetic sample and those reported for the natural product. Herein we describe a total synthesis of polymorphatin A, supported by an X-ray crystal structure of its trimethyl ether, that adds further intrigue as our synthetic sample displays physical and spectral characteristics that differ from data provided in the aforementioned reports.
Biaryl coupling, Bisbibenzyl, Macrocyclic, Nonplanar aromatic, Polymorphatin
Almalki, Faisal Ateeq
099cf883-b9f3-4a16-a4b2-38b272ed3ec4
Sun, Wei
bca29e03-90fc-4684-875e-61d35f1b5cba
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
16 October 2020
Almalki, Faisal Ateeq
099cf883-b9f3-4a16-a4b2-38b272ed3ec4
Sun, Wei
bca29e03-90fc-4684-875e-61d35f1b5cba
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Almalki, Faisal Ateeq, Sun, Wei, Light, Mark and Harrowven, David C.
(2020)
Total synthesis of polymorphatin A, a macrocyclic bisbibenzyl with boat configured arenes.
Tetrahedron, 76 (42), [131521].
(doi:10.1016/j.tet.2020.131521).
Abstract
Polymorphatin A was reported as a constituent of Marchantia polymorpha in 2007 following much speculation as to its likely existence as a natural product. Interest was rekindled when a claimed total synthesis revealed inconsistencies in spectral data between the synthetic sample and those reported for the natural product. Herein we describe a total synthesis of polymorphatin A, supported by an X-ray crystal structure of its trimethyl ether, that adds further intrigue as our synthetic sample displays physical and spectral characteristics that differ from data provided in the aforementioned reports.
Text
Polymorphatin A Tetrahedron for Janice
- Accepted Manuscript
More information
Accepted/In Press date: 14 August 2020
e-pub ahead of print date: 22 August 2020
Published date: 16 October 2020
Keywords:
Biaryl coupling, Bisbibenzyl, Macrocyclic, Nonplanar aromatic, Polymorphatin
Identifiers
Local EPrints ID: 443668
URI: http://eprints.soton.ac.uk/id/eprint/443668
ISSN: 0040-4020
PURE UUID: 1b156b76-6c7d-431d-be74-d33e7f24b2b1
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Date deposited: 08 Sep 2020 16:30
Last modified: 17 Mar 2024 05:51
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Contributors
Author:
Faisal Ateeq Almalki
Author:
Wei Sun
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