Unified Synthetic Strategy for Dendrodolides

  • Author: Veronika Belusa
  • Published Date: 12 April 2015
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Unified Synthetic Strategy for Dendrodolides

Dendrodolides, a class of 12-membered macrolides, were recently isolated from Dendrodochium Sp., a fungus associated with the sea cucumber Holothurian nobilis Selenka, which was collected from the South China Sea. Dendrodolides have different levels of growth-inhibiting activity against human hepatocarcinoma (SMMC-7721) and human colon cancer (HCT116) cells in in-vitro bioassays.

Debendra K. Mohapatra and colleagues, CSIR-Indian Institute of Chemical Technology, Hyderabad, India, have developed a unified synthetic strategy for the total synthesis of the dendrodolide family in a highly convergent and stereoselective manner. The synthetic strategy starts with commercially available materials and involves the enantioselective epoxidation of trans-crotanaldehyde and regioselective opening of an epoxide with a Pd catalyst (Jørgensen asymmetric epoxidation), asymmetric allylation (Keck and Brown allylation), Yamaguchi esterification, and ring-closing metathesis as key steps.

 


 

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