Alkenes with a well defined geometric configuration represent an essential class of key intermediates, and they are a continuous challenge in the synthesis of many natural products and drugs. Different methodologies have been developed, and the Wittig reaction and related transformations for its high level of geometrical control have become the most frequently employed. The counter ion of the base used can be choose in order to obtain different stereoselectivity in Wittig reactions, and in recent years, our efforts are focused on the study of the presence of cerium for a better selectivity towards the formation of (Z)-alkenes. In nature (Z)-alkenes are abundant and capital importance for their biological activity, for this we interested at the synthesis of hydroxyl-substituted alkenylbenzenes because they are effective anticancer agents. Typical component of this family is the (Z)-Climacostol, a toxin belonging to the family of resorcinolic lipids. It is present in prokaryotes as well as in single-celled and multicellular eukaryotes and has attracted great attention due its antimicrobial, cytotoxic and anticancer activities.

Influence of metallic cations in the witting reaction: useful step for the synthesis of anticancer agents

BUONANNO, FEDERICO;ORTENZI, Claudio;
2016

Abstract

Alkenes with a well defined geometric configuration represent an essential class of key intermediates, and they are a continuous challenge in the synthesis of many natural products and drugs. Different methodologies have been developed, and the Wittig reaction and related transformations for its high level of geometrical control have become the most frequently employed. The counter ion of the base used can be choose in order to obtain different stereoselectivity in Wittig reactions, and in recent years, our efforts are focused on the study of the presence of cerium for a better selectivity towards the formation of (Z)-alkenes. In nature (Z)-alkenes are abundant and capital importance for their biological activity, for this we interested at the synthesis of hydroxyl-substituted alkenylbenzenes because they are effective anticancer agents. Typical component of this family is the (Z)-Climacostol, a toxin belonging to the family of resorcinolic lipids. It is present in prokaryotes as well as in single-celled and multicellular eukaryotes and has attracted great attention due its antimicrobial, cytotoxic and anticancer activities.
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