2. Academic Validation
  3. Function-Oriented Synthesis of Pentacyclic Triterpenoids and Discovery of an ent-Estrane as a Natural Product-Inspired Androgen Receptor Antagonist

Function-Oriented Synthesis of Pentacyclic Triterpenoids and Discovery of an ent-Estrane as a Natural Product-Inspired Androgen Receptor Antagonist

  • Org Lett. 2024 Apr 19;26(15):3054-3059. doi: 10.1021/acs.orglett.4c00697.
Zachary D Stempel 1,  Hanna S Radomska 2,  Christopher C Coss 2,  Glenn C Micalizio 1
Affiliations

Affiliations

  • 1 Department of Chemistry, Dartmouth College, Burke Laboratory, Hanover, New Hampshire 03755, United States.
  • 2 Division of Pharmaceutics and Pharmacology, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, United States.
PMID: 38557107 DOI: 10.1021/acs.orglett.4c00697
Abstract

While Pentacyclic Triterpenoids have a rich history in chemistry and biology, the challenges associated with their asymmetric synthesis contribute to the current reality that medicinal exploration in the area is largely constrained to natural product derivatization. To address this deficiency, a function-oriented synthesis of Pentacyclic Triterpenoids was pursued. Overall, we report a divergent synthesis of 26-norgermanicol and 26-norlupeol and we have identified a new class of Androgen Receptor antagonist that is ∼6× more potent than lupeol.

Figures
Products