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In studying the molecular mode of action of naturally occurring compounds such as toxins, the first step is to determine their chemical structure. Unfortunately, such compounds are often in short supply. On page 573, chemist Erick Carreira and his students at ETH Zurich in Switzerland report their synthesis of a complex chlorosulpholipid that has been linked to seafood poisoning and is produced by microalgae isolated from contaminated mussels (Mytilus galloprovincialis). Carreira tells Nature that synthesizing this odd lipid required reliable methods and strategies to be established to assemble its structure.

Why did you choose this toxin?

My group is interested in natural products that have both challenging structures and intriguing biology and chemistry. When I saw these odd-looking structures a few years ago, they instantly caught my interest. Long-chain hydrocarbon lipids are usually relatively unadorned, but these were loaded with chlorides arranged in complex patterns. Little is known about their native biological role and their association with seafood poisoning. I had to work hard to convince students to work on them though, because anticancer agents and neurotoxins are the typical 'hot targets' today.

Was the synthesis more difficult than you expected?

Yes. We knew it would be challenging because the methods for preparing polychlorinated entities were not well-defined. As a result, we encountered some dead ends early on. The most difficult part was figuring out how to position so many chlorides next to each other.

Did overcoming that hurdle create new frontiers for your work?

Absolutely. We initiated a research programme with the aim of better understanding chlorination reactions and the conformational consequences of polychlorinated arrays in hydrocarbons. Now we are trying to establish the structure of other chlorosulpholipids. It will be fun as a chemist to contribute to the narrative of how nature assembles these types of molecule. There is easily enough material for a long-term research programme.

What lessons did you learn during this project?

The project renewed our appreciation that every natural product has an interesting story to tell, and it emphasizes the need to look beyond the accepted criteria by which molecules are judged to be enticing or interesting.