Total Synthesis of (+)-Pancratistatin and Its Potent Topo I Inhibition Activity Studies

Org Lett. 2022 Dec 30;24(51):9458-9462. doi: 10.1021/acs.orglett.2c03888. Epub 2022 Dec 15.

Abstract

As a preeminent anticancer natural product, (+)-pancratistatin has always been a privileged synthetic target. Herein, the total synthesis of (+)-pancratistatin is reported in 10 linear steps by utilizing a known aldehyde as chiral source. This synthetic route features a highly stereoselective intermolecular Michael addition and intramolecular Henry reaction to construct a cyclohexane ring bearing 6 successive stereocenters. Moreover, all of the synthetic steps are reliable and efficient and can be easily scaled up, which facilitated anticancer pharmacological tests of (+)-pancratistatin. Importantly, a new pharmacological mechanism of action was discovered for the first time where (+)-pancratistatin is able to inhibit the activity of topoisomerase I, which would pave the way for the development of new-type Topo I inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amaryllidaceae Alkaloids* / pharmacology
  • Antineoplastic Agents* / pharmacology
  • Isoquinolines / pharmacology

Substances

  • pancratistatin
  • Amaryllidaceae Alkaloids
  • Isoquinolines
  • Antineoplastic Agents