Enabling, Decagram-Scale Synthesis of Macrocyclic MCL-1 Inhibitor ABBV-467

J Org Chem. 2023 Nov 17;88(22):15562-15568. doi: 10.1021/acs.joc.3c00939. Epub 2023 Nov 1.

Abstract

ABBV-467 is a highly potent and selective MCL-1 inhibitor that was advanced to a phase I clinical trial for the treatment of multiple myeloma. Due to its large size and structural complexity, ABBV-467 is a challenging synthetic target. Herein, we describe the synthesis of ABBV-467 on a decagram scale, which enabled preclinical characterization. The strategy is convergent and stereoselective, featuring a hindered biaryl cross coupling, enantioselective hydrogenation, and conformationally preorganized macrocyclization by C-O bond formation as key steps.

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • Hydrogenation
  • Myeloid Cell Leukemia Sequence 1 Protein* / antagonists & inhibitors

Substances

  • Antineoplastic Agents
  • Myeloid Cell Leukemia Sequence 1 Protein