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Synthesis of bicyclo[4.2.0]octane ring of kingianin via [2+2] ketene cycloaddition

Communication

JOURNAL 3124

Organic Communications
VOLUME & ISSUE
Year: 2024 Issue: 1 January-March
PAGES
p.56 - 62
DOI ADDRESS
http://doi.org/10.25135/acg.oc.164.2402.3124
STATISTICS
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AUTHORS
  • Mohamad Nurul Azmi
  • Marc Litaudon
  • Khalijah Awang
  • Yvan Six
PDF OF ARTICLE

GRAPHICAL ABSTRACT

ABSTRACT

Kingianins are pentacyclic polyketides isolated from Endiandra kingiana. They exhibit promising activity in inhibiting anti-apoptotic proteins (i.e Bcl-xL and Mcl-1) and anti-diabetic proteins (α-glucosidase) at micromolar levels. Due to their structural complexity and intriguing biological activity, researchers are increasingly focussing on designing total synthesis routes for these compounds. In this communication, we propose a new non-biomimetic synthesis strategy that utilises a [2+2] ketene cycloaddition reaction as a key-step to access the bicyclo[4.2.0]octane system of kingianins. To the best of our knowledge, this is the first report based on this approach.

 KEYWORDS
  • Kingianins
  • cyclic polyketides
  • bicyclo[4.2.0]octane system
  • [2+2] ketene cycloaddition reaction

SUPPORTING INFORMATION

Supporting Information
Download File A5-164-OC-2402-3124-SI.pdf (2.86 MB)