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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Total Synthesis of Acanthodoral Using a Rearrangement Strategy.

Alina Eggert1, Karl T Schuppe1, Hazel L S Fuchs2

  • 1Institute for Organic Chemistry, Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, Germany.

Organic Letters
|January 2, 2024
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Summary
This summary is machine-generated.

Researchers achieved the second total synthesis of acanthodoral, a marine natural product. This concise three-step synthesis efficiently creates the bicyclo[3.1.1]heptane core and key stereocenters.

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Marine Natural Products

Background:

  • Acanthodoral is a sesquiterpenoid isolated from the marine nudibranch *Acanthodoris nanaimoensis*.
  • The complex structure of acanthodoral, featuring a bicyclo[3.1.1]heptane core and all-carbon quaternary stereocenters, presents a significant synthetic challenge.
  • Only one previous total synthesis of acanthodoral has been reported.

Purpose of the Study:

  • To develop a concise and efficient second total synthesis of (±)-acanthodoral.
  • To establish a synthetic route that effectively constructs the bicyclo[3.1.1]heptane core and the characteristic all-carbon quaternary stereocenters.
  • To explore novel synthetic methodologies for complex natural product assembly.

Main Methods:

  • A three-step synthetic transformation starting from a known precursor.
  • Utilized a samarium(II)-induced 1,2-rearrangement as a key step.
  • Employed a semipinacol rearrangement to facilitate core structure formation.

Main Results:

  • Successfully synthesized (±)-acanthodoral in three steps.
  • Generated a less strained precursor to the bicyclo[3.1.1]heptane core.
  • Constructed both all-carbon quaternary stereocenters crucial to the natural product's structure.

Conclusions:

  • The presented synthetic route is a highly efficient and concise method for accessing acanthodoral.
  • The employed rearrangement reactions proved pivotal in constructing the challenging molecular architecture.
  • This synthesis provides a valuable alternative pathway for the preparation of this marine natural product.