A new route to platencin via decarboxylative radical cyclization

Chem Commun (Camb). 2014 Dec 25;50(99):15706-9. doi: 10.1039/c4cc07316a. Epub 2014 Oct 31.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminophenols / chemical synthesis
  • Aminophenols / chemistry*
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Decarboxylation
  • Dioxanes / chemistry
  • Free Radicals / chemistry*
  • Molecular Conformation
  • Organometallic Compounds / chemistry*
  • Polycyclic Compounds / chemical synthesis
  • Polycyclic Compounds / chemistry*
  • Pyridines / chemistry
  • Streptomyces / chemistry
  • Streptomyces / metabolism

Substances

  • Aminophenols
  • Anti-Bacterial Agents
  • Biological Products
  • Dioxanes
  • Free Radicals
  • Organometallic Compounds
  • Polycyclic Compounds
  • Pyridines
  • 1,4-dioxane
  • pyridine
  • platencin