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Concise Total Synthesis of (+)-Bionectins A and C.

Alexis Coste1, Justin Kim, Timothy C Adams

  • 1Massachusetts Institute of Technology, Department of Chemistry, 77 Massachusetts Avenue 18-292, Cambridge, MA 02139-4307, USA. movassag@mit.edu.

Chemical Science
|July 24, 2013
PubMed
Summary

This study presents an efficient total synthesis of (+)-bionectins A and C, introducing novel methods for amino acid synthesis and epipolythiodiketopiperazine construction. Key discoveries include stereoinvertive hydroxylation and direct triketopiperazine synthesis.

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis

Background:

  • Epipolythiodiketopiperazines (ETPs) are a class of natural products with diverse biological activities.
  • The total synthesis of complex natural products like (+)-bionectins A and C presents significant challenges.

Purpose of the Study:

  • To achieve the concise and efficient total synthesis of (+)-bionectins A and C.
  • To develop scalable and novel synthetic methodologies applicable to ETPs and related compounds.

Main Methods:

  • Development of a scalable synthesis for *erythro*-β-hydroxytryptophan.
  • Application of an intramolecular Friedel-Crafts reaction for indole functionalization.
  • Introduction of a new mercaptan reagent for mild ETP ring formation and cleavage.

Main Results:

  • Successful total synthesis of (+)-bionectin A and C.
  • Demonstration of a novel intramolecular Friedel-Crafts indolylation.
  • First report of permanganate-mediated stereoinvertive hydroxylation of diketopiperazine α-stereocenters.
  • First synthesis of a triketopiperazine directly from a *cyclo*-dipeptide.

Conclusions:

  • The developed synthetic strategies are efficient and scalable.
  • New insights into the chemistry of ETPs and diketopiperazines were gained.
  • The synthesis and X-ray analysis of (+)-bionectin A prompted reevaluation of its original characterization.