Building molecular complexity from scratch

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Science  26 Aug 2016:
Vol. 353, Issue 6302, pp. 866-867
DOI: 10.1126/science.aah5871

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Cycloaddition reactions convert simple unsaturated components into cyclic products. Because cyclic molecules are intrinsically more complex than linear ones, cycloaddition reactions are ideally suited for building molecular complexity that characterizes many natural products used as pharmaceuticals. The equivalent to the Diels-Alder reaction for forming six-membered rings in the construction of five-membered rings is the Pauson-Khand reaction, a [2+2+1] cycloaddition reaction between an alkene, an alkyne, and carbon monoxide. On page 912 of this issue, Chuang et al. (1) have used a rhodium-catalyzed Pauson-Khand reaction to assemble the tetracyclic core of (+)-ryanodol in an elegant 15-step synthesis.