A new route to platencin via decarboxylative radical cyclization

Gamal A.I. Moustafa; Yuki Saku; Hiroshi Aoyama; Takehiko Yoshimitsu

doi:10.1039/c4cc07316a

A new route to platencin via decarboxylative radical cyclization

Gamal A.I. Moustafa, Yuki Saku, Hiroshi Aoyama, Takehiko Yoshimitsu

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	15706-15709
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	99
DOIs	https://doi.org/10.1039/c4cc07316a
Publication status	Published - Nov 18 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c4cc07316a

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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.",

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AU - Moustafa, Gamal A.I.

AU - Saku, Yuki

AU - Aoyama, Hiroshi

AU - Yoshimitsu, Takehiko

PY - 2014/11/18

Y1 - 2014/11/18

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AB - 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.

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ER -

A new route to platencin via decarboxylative radical cyclization

Abstract

ASJC Scopus subject areas

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