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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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Total synthesis of (±)-dragmacidin E.

Ken S Feldman1, Paiboon Ngernmeesri

  • 1Chemistry Department, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu

Organic Letters
|October 1, 2011
PubMed
Summary

Researchers synthesized the bis indole sponge alkaloid dragmacidin E using a 25-step process. Key steps involved Witkop cyclization and cyclodehydrative pyrazinone synthesis to construct the complex molecule.

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis

Background:

  • Dragmacidin E is a bis indole alkaloid found in marine sponges.
  • Bis indole alkaloids represent a class of compounds with potential biological activities.

Purpose of the Study:

  • To achieve the total synthesis of dragmacidin E.
  • To develop a synthetic route for complex bis indole alkaloids.

Main Methods:

  • A 25-step synthesis was employed starting from 7-benzhydroxyindole.
  • Key reactions included Witkop cyclization for seven-membered ring formation.
  • A cyclodehydrative pyrazinone synthesis was utilized to couple indole sectors.

Main Results:

  • The racemic form of dragmacidin E was successfully synthesized.

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  • The synthetic route demonstrated the feasibility of constructing the dragmacidin E core structure.

    • Conclusions:

    • The total synthesis of dragmacidin E was accomplished.
    • The developed synthetic strategy provides a pathway for accessing related bis indole alkaloids.