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

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-12, Vol.82 (24), p.13051-13067
Main Authors: Roizen, Jennifer L, Jones, Amanda C, Smith, Russell C, Virgil, Scott C, Stoltz, Brian M
Format: Article
Language:English
Subjects:
Alkenes - chemistry
chemical reactions
chemical structure
Cyclization
Diterpenes - chemistry
Lactones - chemistry
Models, Biological
Molecular Structure
organic chemistry
organic compounds
Propane - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.7b02030