Synthesis of Spongidine A and D and Petrosaspongiolide L Methyl Ester Using Pyridine C-H Functionalization

Org Lett. 2020 Jan 17;22(2):552-555. doi: 10.1021/acs.orglett.9b04315. Epub 2019 Dec 26.

Abstract

An efficient strategy for the synthesis of the potent phospholipase A2 inhibitors spongidine A and D is presented. The tetracyclic core of the natural products was assembled via an intramolecular hydrogen atom transfer initiated Minisci reaction. A divergent late-stage functionalization of the tetracyclic ring system was also used to achieve a concise synthesis of petrosaspongiolide L methyl ester.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Oleanolic Acid / chemical synthesis*
  • Oleanolic Acid / chemistry
  • Pyridines / chemistry*
  • Stereoisomerism

Substances

  • Pyridines
  • Oleanolic Acid
  • pyridine