A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ

Wan Shin Kim, Zachary A. Shalit, Sidney M. Nguyen, Emmalie Schoepke, Alan Eastman, Thomas P. Burris, Arti B. Gaur () and Glenn C. Micalizio ()
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Wan Shin Kim: Burke Laboratory
Zachary A. Shalit: Burke Laboratory
Sidney M. Nguyen: Dartmouth College, Geisel School of Medicine, Department of Neurology
Emmalie Schoepke: Washington University School of Medicine and St. Louis College of Pharmacy
Alan Eastman: Dartmouth College, Geisel School of Medicine, Department of Molecular and Systems Biology
Thomas P. Burris: Washington University School of Medicine and St. Louis College of Pharmacy
Arti B. Gaur: Dartmouth College, Geisel School of Medicine, Department of Neurology
Glenn C. Micalizio: Burke Laboratory

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Natural product and natural product-like molecules continue to be important for the development of pharmaceutical agents, as molecules in this class play a vital role in the pipeline for new therapeutics. Among these, tetracyclic terpenoids are privileged, with >100 being FDA-approved drugs. Despite this significant pharmaceutical success, there remain considerable limitations to broad medicinal exploitation of the class due to lingering scientific challenges associated with compound availability. Here, we report a concise asymmetric route to forging natural and unnatural (enantiomeric) C19 and C20 tetracyclic terpenoid skeletons suitable to drive medicinal exploration. While efforts have been focused on establishing the chemical science, early investigations reveal that the emerging chemical technology can deliver compositions of matter that are potent and selective agonists of the estrogen receptor beta, and that are selectively cytotoxic in two different glioblastoma cell lines (U251 and U87).

Date: 2019
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DOI: 10.1038/s41467-019-10415-6

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