Radical cyclization strategies in total syntheses of bioactive fused cyclic natural products

Research output: Contribution to journalReview article

Abstract

The present article discusses our recent endeavors on natural product syntheses wherein radical reactions are strategically employed to access fused carbocycles. Particular emphasis is placed on the radical cyclizations that made it possible to establish the unique bond connectivity and functionalities of the target natural products. The radical chemistry-based approaches to platencin and clavilactone B are discussed here to show the utility of titanocene(III)-mediated epoxy enone cyclization, decarboxylative radical cyclization of an alkynyl carboxylic acid derivative with lead(IV) in 1,4-dioxane, and samarium(II)-mediated radical cyclization-fragmentation of an unsaturated keto ester, all of which serve as versatile means to elaborate the natural products.

Original languageEnglish
Pages (from-to)350-359
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume74
Issue number4
Publication statusPublished - 2016
Externally publishedYes

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Cyclization
Biological Products
Samarium
Carboxylic Acids
Esters
Derivatives

Keywords

  • Bioactive natural products
  • Decarboxylation
  • Fragmentation
  • Hydrogen transfer
  • Lead tetraacetate
  • Radical cyclization
  • Samarium diiodide
  • Titanocene (III) chloride
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "The present article discusses our recent endeavors on natural product syntheses wherein radical reactions are strategically employed to access fused carbocycles. Particular emphasis is placed on the radical cyclizations that made it possible to establish the unique bond connectivity and functionalities of the target natural products. The radical chemistry-based approaches to platencin and clavilactone B are discussed here to show the utility of titanocene(III)-mediated epoxy enone cyclization, decarboxylative radical cyclization of an alkynyl carboxylic acid derivative with lead(IV) in 1,4-dioxane, and samarium(II)-mediated radical cyclization-fragmentation of an unsaturated keto ester, all of which serve as versatile means to elaborate the natural products.",
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AB - The present article discusses our recent endeavors on natural product syntheses wherein radical reactions are strategically employed to access fused carbocycles. Particular emphasis is placed on the radical cyclizations that made it possible to establish the unique bond connectivity and functionalities of the target natural products. The radical chemistry-based approaches to platencin and clavilactone B are discussed here to show the utility of titanocene(III)-mediated epoxy enone cyclization, decarboxylative radical cyclization of an alkynyl carboxylic acid derivative with lead(IV) in 1,4-dioxane, and samarium(II)-mediated radical cyclization-fragmentation of an unsaturated keto ester, all of which serve as versatile means to elaborate the natural products.

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