A concise total synthesis of deoxyschizandrin and exploration of its antiproliferative effects and those of structurally related derivatives.

Abstract

The natural product deoxyschizandrin has been shown to have a wide range of biological activities. In recent years the therapeutic potential of this compound against cancers has attracted significant interest. Herein we describe a concise de novo total synthesis of deoxyschizandrin based around a double organocuprate oxidation strategy. In addition, we present the results of biological studies exploring the ability of deoxyschizandrin and synthetic precursors lacking the medium ring biaryl unit to inhibit the proliferation of a human cancer cell line. These studies led to the identification of a structurally novel agent with in vitro anticancer activity.

• Authors: Shaojun Zheng, Sarah J Aves, Luca Laraia, Warren R J D Galloway, Kurt G Pike, Wenjun Wu, David R Spring
• Journal: Chemistry (Weinheim an der Bergstrasse, Germany) (Chemistry) Vol. 18 Issue 11 Pg. 3193-8 (Mar 12 2012) ISSN: 1521-3765 [Electronic] Germany
• PMID: 22307955 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Antineoplastic Agents, Phytogenic
• Cyclooctanes
• Lignans
• Polycyclic Compounds
• schizandrin A

Topics

• Antineoplastic Agents, Phytogenic (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cyclooctanes (chemical synthesis, chemistry, pharmacology)
• Drug Screening Assays, Antitumor
• Humans
• Lignans (chemical synthesis, chemistry, pharmacology)
• Molecular Structure
• Polycyclic Compounds (chemical synthesis, chemistry, pharmacology)