Premium
Enantioselective Divergent Syntheses of Several Polyhalogenated Plocamium Monoterpenes and Evaluation of Their Selectivity for Solid Tumors
Author(s) -
Vogel Carl V.,
Pietraszkiewicz Halina,
Sabry Omar M.,
Gerwick William H.,
Valeriote Frederick A.,
Vanderwal Christopher D.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407726
Subject(s) - enantioselective synthesis , chemistry , selectivity , blueprint , monoterpene , stereochemistry , enantiomer , terpene , combinatorial chemistry , organic chemistry , catalysis , mechanical engineering , engineering
The family of polyhalogenated monoterpenes from Plocamium counts over a hundred known members. Using glyceraldehyde acetonide as a chiral‐pool precursor, an enantioselective and divergent strategy was developed that provides a blueprint for the synthesis of many of the small yet complex acyclic members of this family. The broad applicability of this approach is demonstrated with the short, eight‐step synthesis of four natural products and three analogues. These syntheses are the first of any members of the acyclic polyhalogenated Plocamium monoterpenes and permitted the evaluation of their selectivity against a range of tumor cell lines.