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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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A Total Synthesis of (-)-Strychnine Using Photoredox Catalysis.

Rainer Wiechert1, Leander Geske1, Jasmin Hammes1

  • 1Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, Mainz 55128, Germany.

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PubMed
Summary

This study presents a concise synthetic route to (-)-strychnine using photoredox catalysis and a convergent cascade reaction. The method utilizes renewable building blocks for efficient synthesis of this complex alkaloid.

Keywords:
AlkaloidsCascade cyclizationPhotoredox catalysisRadical reactionsTotal synthesis

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Total Synthesis

Background:

  • Strychnine is a complex indole alkaloid with significant pharmacological properties.
  • Previous syntheses of strychnine are often lengthy and challenging.
  • Developing efficient and sustainable routes to strychnine is of great interest.

Purpose of the Study:

  • To develop a concise and efficient synthetic route to (-)-strychnine.
  • To employ modern synthetic methodologies, including photoredox catalysis.
  • To utilize building blocks derived from renewable resources.

Main Methods:

  • Photoredox-catalytic C2-cyanomethylation of Boc-l-Trp-OMe.
  • A condensation-electrocyclization cascade reaction for fragment coupling.
  • Photochemical decarboxylation and subsequent transformations.

Main Results:

  • A convergent synthesis of an advanced intermediate toward (-)-strychnine was achieved.
  • Strychnofluorine was accessed via photochemical decarboxylation.
  • The Wieland-Gumlich aldehyde was formed, leading to (-)-strychnine.
  • All starting materials were derived from renewable sources.

Conclusions:

  • The presented route offers a concise and efficient pathway to (-)-strychnine.
  • The synthesis highlights the utility of photoredox catalysis and cascade reactions in complex molecule synthesis.
  • The use of renewable resources aligns with green chemistry principles.