A new route to platencin via decarboxylative radical cyclization

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

Research output: Contribution to journalArticle

7 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 languageEnglish
Pages (from-to)15706-15709
Number of pages4
JournalChemical Communications
Volume50
Issue number99
DOIs
Publication statusPublished - Dec 25 2014
Externally publishedYes

Fingerprint

Cyclization
Esterification
Antibiotics
Biological Products
Pyridine
Esters
Carbon
Lead
Anti-Bacterial Agents
Decarboxylation
pyridine
1,4-dioxane
platencin

ASJC Scopus subject areas

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

Cite this

A new route to platencin via decarboxylative radical cyclization. / Moustafa, Gamal A.I.; Saku, Yuki; Aoyama, Hiroshi; Yoshimitsu, Takehiko.

In: Chemical Communications, Vol. 50, No. 99, 25.12.2014, p. 15706-15709.

Research output: Contribution to journalArticle

Moustafa, Gamal A.I. ; Saku, Yuki ; Aoyama, Hiroshi ; Yoshimitsu, Takehiko. / A new route to platencin via decarboxylative radical cyclization. In: Chemical Communications. 2014 ; Vol. 50, No. 99. pp. 15706-15709.
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