Work

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

Year: 2017

Type: article

Abstract: 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.7b02030

Authors: Jennifer L. Roizen, Amanda C. Jones, Russell C. Smith, Scott C. Virgil, Brian M. Stoltz

Institution: California Institute of Technology

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green