Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning

Christian Nilewski, Roger W. Geisser and Erick M. Carreira ()
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Christian Nilewski: Laboratorium für Organische Chemie, ETH Zürich, CH-8093 Zürich, Switzerland
Roger W. Geisser: Laboratorium für Organische Chemie, ETH Zürich, CH-8093 Zürich, Switzerland
Erick M. Carreira: Laboratorium für Organische Chemie, ETH Zürich, CH-8093 Zürich, Switzerland

Nature, 2009, vol. 457, issue 7229, 573-576

Abstract: A cytotoxin synthesized Seafood poisoning can be caused by a number of toxins, including the chlorosulpholipids. These molecules are particularly intriguing because of their structural and stereochemical complexity, and because their mechanism of biological action remains unknown. The limited availability of these natural products has made in-depth biochemical studies difficult. Now the first total synthesis of a chlorosulpholipid cytotoxin is reported, opening the way to full pharmacological characterization and the proper evaluation of the risk for human health. The synthesis confirms the structure proposed for the chlorosulpholipids, and one of the early discoveries is the unanticipated reactivity of polychlorinated hydrocarbons within the molecule.

Date: 2009
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DOI: 10.1038/nature07734

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