Premium
A Concise Total Synthesis of Deoxyschizandrin and Exploration of Its Antiproliferative Effects and those of Structurally Related Derivatives
Author(s) -
Zheng Shaojun,
Aves Sarah J.,
Laraia Luca,
Galloway Warren R. J. D.,
Pike Kurt G.,
Wu Wenjun,
Spring David R.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103530
Subject(s) - natural product , in vitro , total synthesis , stereochemistry , chemistry , combinatorial chemistry , cancer cell lines , ring (chemistry) , computational biology , biology , biochemistry , cancer , cancer cell , organic chemistry , genetics
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.