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

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.

SUBMITTER: Roizen JL

PROVIDER: S-EPMC5732049 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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

Roizen Jennifer L JL Jones Amanda C AC Smith Russell C RC Virgil Scott C SC Stoltz Brian M BM

The Journal of organic chemistry 20171121 24

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. Addit ...[more]

PMID: 29111725

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Enantioselective, Convergent Synthesis of the Ineleganolide Core by a Tandem Annulation Cascade.

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Correction: Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade.

Project description:[This corrects the article DOI: 10.1039/C6SC03347D.].

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Diastereoselective Indole-Dearomative Cope Rearrangements by Compounding Minor Driving Forces.

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A Tandem Iridium-Catalyzed "Chain-Walking"/Cope Rearrangement Sequence.

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