Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization-Cope or Cyclopropanation-Cope Rearrangements as Key Steps.


Journal Article

Recently, we reported a convergent cyclopropanation-Cope approach to the core of ineleganolide, which was the first disclosed synthesis of the core of the norditerpene natural product ineleganolide. In this complementary work, a model system for the core of ineleganolide has been prepared through a series of tandem cyclopropanation-Cope and translactonization-Cope rearrangements. Work with this model system has enriched our understanding of the cyclopropanation-Cope rearrangement sequence. Additionally, research into this model system has driven the development of tandem translactonization-Cope rearrangements.

Full Text

Duke Authors

Cited Authors

  • Roizen, JL; Jones, AC; Smith, RC; Virgil, SC; Stoltz, BM

Published Date

  • December 2017

Published In

Volume / Issue

  • 82 / 24

Start / End Page

  • 13051 - 13067

PubMed ID

  • 29111725

Pubmed Central ID

  • 29111725

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 1520-6904

Digital Object Identifier (DOI)

  • 10.1021/acs.joc.7b02030


  • eng