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Synthetic studies towards cryptolaevilactone M from d-glucose.

Anjali Sharma1, Dhananjoy Mondal1, Smritilekha Bera1

  • 1School of Chemical Sciences, Central University of Gujarat, Vadodara, 391107, India.

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|February 24, 2026
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Summary

Researchers synthesized cryptolaevilactone M using a ten-step strategy starting from D-(+)-glucose. This novel approach efficiently builds the core structure, paving the way for related bioactive molecules.

Keywords:
Cryptolaevilactone MIndium-mediated allylationNatural product synthesisO-AcryloylationRing-closing metathesisStereoselective synthesisα,β-unsaturated δ-lactones

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis

Background:

  • Cryptolaevilactone M is a bioactive natural product.
  • Efficient synthetic routes to complex lactones are valuable.

Purpose of the Study:

  • To develop a synthetic strategy for cryptolaevilactone M from D-(+)-glucose.
  • To establish a versatile route for related δ-lactones.

Main Methods:

  • Ten-step synthesis starting with C-3 PMB protected d-glucose diacetonide.
  • Diastereoselective indium-mediated allylation and Grubbs II-catalyzed ring-closing metathesis.
  • Selective anomeric oxidation and Grignard addition to construct the core framework.

Main Results:

  • Successful construction of the α,β-unsaturated δ-lactone core.
  • High yields achieved in key steps like allylation (94%) and ring-closing metathesis (92%).
  • Introduction of the phenyl 1-butene side chain via Grignard addition, establishing the core framework.

Conclusions:

  • The developed synthetic strategy provides efficient access to cryptolaevilactone M.
  • The route is versatile for synthesizing related bioactive δ-lactones.
  • Further steps are underway to complete the synthesis of cryptolaevilactone M.