Divergent synthesis of cytotoxic styryl lactones from D-xylose. The first total synthesis of (+)-crassalactone C

Org Lett. 2007 Oct 11;9(21):4235-8. doi: 10.1021/ol701734s. Epub 2007 Sep 15.

Abstract

A new divergent approach to (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2), as well as the first total synthesis of crassalactone C (3), has been achieved starting from D-xylose. In a preliminary bioassay, all three natural products 1, 2, and 3 showed remarkable in vitro antiproliferative activities against K562, Raji, and HeLa neoplastic cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Annonaceae / chemistry
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Lactones / pharmacology
  • Molecular Structure
  • Plants, Medicinal / chemistry
  • Tumor Cells, Cultured
  • Xylose / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Lactones
  • crassalactone C
  • 7-goniofufurone
  • Xylose