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Total synthesis of polymorphatin A, a macrocyclic bisbibenzyl with boat configured arenes

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
0040-4020
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
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).

Record type: Article

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
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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
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 08 Sep 2020 16:30
Last modified: 04 Mar 2021 02:35

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Contributors

Author: Faisal Ateeq Almalki
Author: Wei Sun
Author: Mark Light ORCID iD

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