Scopariusicides, Novel Unsymmetrical Cyclobutanes: Structural Elucidation and Concise Synthesis by a Combination of Intermolecular [2 + 2] Cycloaddition and C-H Functionalization

Org Lett. 2015 Dec 18;17(24):6062-5. doi: 10.1021/acs.orglett.5b03079. Epub 2015 Nov 29.

Abstract

Scopariusicides A (1) and B (2), two novel immunosuppressive unsymmetrical cyclobutane derivatives, were isolated from the aerial parts of Isodon scoparius. Moreover, based on the results of phytochemical investigation, a concise stereocontrolled synthesis of scopariusicide A and its analogues with enhanced biological activities was efficiently achieved using the main diterpenoid (3) isolated from this plant as a readily available starting material. A crossed intermolecular [2 + 2] photocycloaddition and a Pd-catalyzed sp(3) C-H bond β-arylation were used synergistically to access the highly congested unsymmetrical cyclobutane core with four contiguous stereocenters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cycloaddition Reaction
  • Cyclobutanes / chemical synthesis*
  • Cyclobutanes / chemistry
  • Cyclobutanes / pharmacology
  • Drug Discovery
  • Humans
  • Immunosuppressive Agents / chemical synthesis*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology
  • Isodon / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism
  • T-Lymphocytes / drug effects

Substances

  • Cyclobutanes
  • Immunosuppressive Agents
  • scopariusicide A
  • scopariusicide B