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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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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 Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Updated: Sep 17, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Total Syntheses of (±)-Lepadiformine B and C.

Wei-Ting Hsiao1, Jui-Lin Wu1, Wen-Hua Chiou1

  • 1Department of Chemistry, National Chung-Hsing University, Taichung 402 ,Taiwan, ROC.

The Journal of Organic Chemistry
|July 4, 2025
PubMed
Summary

This study presents the total synthesis of lepadiformine B and C. The novel approach achieves stereodivergent synthesis of key intermediates for complex molecule construction.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Natural Product Synthesis

Background:

  • Lepadiformines are marine alkaloids with potential biological activity.
  • Developing efficient synthetic routes to complex alkaloids is crucial for further investigation.

Purpose of the Study:

  • To achieve the total synthesis of (±)-lepadiformine B and C.
  • To develop a stereodivergent synthetic strategy for decahydroquinoline derivatives.

Main Methods:

  • Stereodivergent synthesis of cis- and trans-N-acetyl-2-alkyl-8a-cyanodecahydroquinoline via deprotection-initiated alkylative/reductive cyclization.
  • Dieckmann-type condensation to a tricyclic lactam.
  • Iridium-catalyzed reductive cyanation, hydrolysis, reduction, and Bruylants reactions.

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Main Results:

  • Successful total syntheses of (±)-lepadiformine B and C.
  • Demonstration of a stereodivergent approach to key decahydroquinoline intermediates.
  • Efficient construction of the complex tricyclic lactam core.

Conclusions:

  • The developed synthetic strategy provides access to lepadiformine B and analogues.
  • The stereodivergent synthesis of decahydroquinolines is a valuable tool for natural product synthesis.