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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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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
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Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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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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Synthesis and Structural Reassignment of Pubescone.

Koichiro Ota1, Shinnosuke Okazaki1, Hiroaki Miyaoka1

  • 1School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

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|April 29, 2026
PubMed
Summary

Pubescone, a plant-derived compound, has been structurally misidentified for over a decade. This study confirms pubescone is actually saniculamoid D through total synthesis and spectroscopic analysis.

Keywords:
bicyclic terpenoidpubesconesaniculamoid Dstructural reassignmenttotal synthesis

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Area of Science:

  • Natural Product Chemistry
  • Organic Synthesis
  • Spectroscopic Analysis

Background:

  • Pubescone, isolated since 2010, was initially characterized with a unique 11(7→6)abeo-14-norcarabrane skeleton.
  • Recent total synthesis of saniculamoid D revealed spectroscopic similarities to pubescone, raising questions about pubescone's structure.

Purpose of the Study:

  • To investigate the structural misidentification of pubescone.
  • To clarify the identity of the natural product previously known as pubescone.

Main Methods:

  • Total synthesis of the proposed pubescone structure.
  • Comparison of spectroscopic data (13C-NMR, specific rotation) between synthetic compounds and natural products.
  • Detailed analysis of NMR and specific rotation data.

Main Results:

  • The synthesized pubescone structure showed significant discrepancies with reported natural product data.
  • Synthetic (4S,5S,6S,10S)-saniculamoid D exhibited excellent agreement with the reported data for natural pubescone.
  • The structural misidentification of pubescone has persisted for over 10 years.

Conclusions:

  • The originally proposed structure of pubescone is incorrect.
  • Natural pubescone is conclusively identified as saniculamoid D.
  • Total synthesis is crucial for validating complex natural product structures and correcting misidentifications.