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

Velimir Popsavin; Goran Benedeković; Bojana Srećo; Mirjana Popsavin; Jovana Francuz; Vesna Kojić; Gordana Bogdanović

doi:10.1021/ol701734s

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.

Authors

Velimir Popsavin¹, Goran Benedeković, Bojana Srećo, Mirjana Popsavin, Jovana Francuz, Vesna Kojić, Gordana Bogdanović

Affiliation

¹ Department of Chemistry, Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 3, 21000 Novi Sad, Serbia. [email protected]

PMID: 17867695
DOI: 10.1021/ol701734s

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