A new route to platencin via decarboxylative radical cyclization
A new route to platencin via decarboxylative radical cyclization
A new approach to platencin, a potent antibiotic isolated from Streptomyces platensis, has been established. The highly congested tricyclic core of the natural product was successfully constructed by decarboxylative radical cyclization of an alkynyl silyl ester with Pb(OAc)4 in the presence of pyridine in refluxing 1,4-dioxane. The key decarboxylation, which likely takes place via lead(IV) esterification followed by carbon-centered radical generation and subsequent capture of the radical with a triple bond, allows the rapid construction of the twisted polycyclic system.
15706-15709
Moustafa, Gamal A. I.
1a452cdc-4856-4243-9864-b391fb115f07
Saku, Yuki
69396651-b99f-446a-885f-4bc079496b1b
Aoyama, Hiroshi
e1cc97e2-a1d4-4125-9ada-858a412e8097
Yoshimitsu, Takehiko
1e9f0d2b-3870-4c7c-aca6-171a4ede5548
2014
Moustafa, Gamal A. I.
1a452cdc-4856-4243-9864-b391fb115f07
Saku, Yuki
69396651-b99f-446a-885f-4bc079496b1b
Aoyama, Hiroshi
e1cc97e2-a1d4-4125-9ada-858a412e8097
Yoshimitsu, Takehiko
1e9f0d2b-3870-4c7c-aca6-171a4ede5548
Moustafa, Gamal A. I., Saku, Yuki, Aoyama, Hiroshi and Yoshimitsu, Takehiko
(2014)
A new route to platencin via decarboxylative radical cyclization.
Chemical Communications, 50 (99), .
(doi:10.1039/C4CC07316A).
Abstract
A new approach to platencin, a potent antibiotic isolated from Streptomyces platensis, has been established. The highly congested tricyclic core of the natural product was successfully constructed by decarboxylative radical cyclization of an alkynyl silyl ester with Pb(OAc)4 in the presence of pyridine in refluxing 1,4-dioxane. The key decarboxylation, which likely takes place via lead(IV) esterification followed by carbon-centered radical generation and subsequent capture of the radical with a triple bond, allows the rapid construction of the twisted polycyclic system.
This record has no associated files available for download.
More information
Accepted/In Press date: 23 October 2014
Published date: 2014
Identifiers
Local EPrints ID: 427463
URI: http://eprints.soton.ac.uk/id/eprint/427463
ISSN: 1359-7345
PURE UUID: ecd136a4-f2d2-4419-a1b4-282e94c3cf51
Catalogue record
Date deposited: 17 Jan 2019 17:30
Last modified: 16 Mar 2024 04:40
Export record
Altmetrics
Contributors
Author:
Yuki Saku
Author:
Hiroshi Aoyama
Author:
Takehiko Yoshimitsu
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
