Modular total synthesis of lamellarin D

J Org Chem. 2005 Sep 30;70(20):8231-4. doi: 10.1021/jo051083a.

Abstract

[Chemical reaction: see text] A modular total synthesis of lamellarin D, a marine alkaloid with potent cytotoxic as well as topoisomerase I inhibition properties, has been accomplished. A sequential and regioselective bromination/Suzuki cross-coupling procedure was applied for the introduction of aryl groups at positions 1 and 2 of scaffold 1. Microwave-assisted 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidation to yield pyrroloisoquinoline 15, followed by phenol group deprotection and subsequent lactonization, gave lamellarin D (18% in eight steps from 1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Dioxanes
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Indicators and Reagents
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Models, Molecular
  • Topoisomerase I Inhibitors

Substances

  • Alkaloids
  • Coumarins
  • Dioxanes
  • Enzyme Inhibitors
  • Heterocyclic Compounds, 4 or More Rings
  • Indicators and Reagents
  • Isoquinolines
  • Topoisomerase I Inhibitors
  • lamellarin D
  • 1,4-dioxane