4.7 Article

Stereoselective synthesis of the Paulownia bagworm sex pheromone

Journal

CHINESE CHEMICAL LETTERS
Volume 28, Issue 3, Pages 558-562

Publisher

ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2016.11.018

Keywords

Pheromone Paulownia bagworm; Evans template; Total synthesis

Funding

  1. National Natural Science Foundation of China [31301712]
  2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

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According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5+C7+C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li2CuCl4 was effectively employed in the Csp(3) -Csp(3) coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

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