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First synthesis of (±)-halichonadins A-D.

Ryohei Fujita1, Kaito Ooka1, Hiroaki Wasada2

  • 1Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.

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Researchers achieved the first total synthesis of marine isocyanide terpene (±)-halichonadin C. This breakthrough utilized a novel hypervalent iodine-promoted Hofmann rearrangement for isocyanide construction.

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Marine Natural Products

Background:

  • Marine natural products, such as halichonadins, exhibit unique chemical structures and biological activities.
  • The total synthesis of complex molecules like (±)-halichonadin C presents significant chemical challenges.
  • Isocyanide functional groups are rare in natural products and their synthetic introduction is often difficult.

Purpose of the Study:

  • To achieve the first total synthesis of the marine isocyanide terpene (±)-halichonadin C.
  • To develop a novel synthetic strategy for constructing the isocyanide moiety.
  • To explore the biosynthetic pathways of halichonadins A-D.

Main Methods:

  • Total synthesis of (±)-halichonadin C.
  • Nitrile-to-isocyanide interconversion using hypervalent iodine-promoted Hofmann rearrangement.
  • Transformation of (±)-halichonadin C to related natural products.

Main Results:

  • Successful first total synthesis of (±)-halichonadin C.
  • Efficient construction of the isocyanide group at a sterically hindered position (C-6).
  • Conversion of (±)-halichonadin C to halichonadins A and B via a proposed biosynthetic intermediate.

Conclusions:

  • The developed synthetic strategy is effective for accessing complex isocyanide-containing natural products.
  • The synthesis provides insights into the biosynthesis of the halichonadin family.
  • This work expands the synthetic toolbox for incorporating isocyanide functionalities.