4.8 Article

Catalysis Driven Six-Step Synthesis of Apratoxin A Key Polyketide Fragment

Journal

ORGANIC LETTERS
Volume 24, Issue 36, Pages 6537-6542

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02482

Keywords

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Funding

  1. Agence National de la Recherche [ANR-19-CE07-0033]
  2. Centre National de la Recherche Scientifique (CNRS)
  3. Aix-Marseille Universite
  4. China Scholarship Council [201908070004]
  5. Agence Nationale de la Recherche (ANR) [ANR-19-CE07-0033] Funding Source: Agence Nationale de la Recherche (ANR)

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Apratoxin A is a potent anticancer natural product. The synthesis of its key compound has always been a challenge in organic chemistry. By combining different catalytic reactions, the key polyketide fragment can be prepared rapidly. This method allows for the preparation of the apratoxin A fragment in just six steps, representing the shortest route to this polyketide.
Apratoxin A is a potent anticancer natural product whose key polyketide fragment constitutes a considerable challenge for organic synthesis, with five prior syntheses requiring 12 to 20 steps for its preparation. By combining different redoxeconomical catalytic stereoselective transformations, the key polyketide fragment could be rapidly prepared. Followed by a site selective protection of the diol, this strategy enables the preparation of the apratoxin A fragment in only six steps, representing the shortest route to this polyketide.

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