4.8 Article

Total Synthesis and Determination of the Absolute Configuration of Rakicidin C

Journal

ORGANIC LETTERS
Volume 23, Issue 18, Pages 7069-7073

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02476

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Funding

  1. National Natural Science Foundation of China [U1801288]
  2. National Science Fund for Distinguished Young Scholars [81625021]
  3. Fundamental Research Funds for the Central Universities
  4. Hundred Young Academic Leaders Program of Nankai University
  5. Natural Science the Frontiers Science Center for New Organic Matter [63181206]

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The absolute configuration of rakicidin C was predicted using optical rotation data and compared with APD-cyclic depsipeptides, and then confirmed through total synthesis. The synthesis route involved 19 longest linear steps with an overall yield of 1.49%, determining the configuration of five chiral centers as 2R, 15R, 16R, 17S, and 19S.
The absolute configuration of rakicidin C was predicted by comparison of optical rotation data and absolute configuration of APD-cyclic depsipeptides and further determined by total synthesis. The absolute configuration of five chiral centers was determined as 2R, 15R, 16R, 17S, and 19S. Our efficient route involves 19 longest linear steps with an overall yield of 1.49%.

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