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.
- A Unified Synthetic Strategy for Dendrodolides E, F, G, I, J, and L,
Debendra K. Mohapatra, D. Prabhakar Reddy, Srinivas Gajula, Karthik Pulluri, J. S. Yadav,
Asian J. Org. Chem. 2015.