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Total synthesis reveals atypical atropisomerism in a small-molecule natural product, tryptorubin A

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Science  24 Jan 2020:
Vol. 367, Issue 6476, pp. 458-463
DOI: 10.1126/science.aay9981

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A twisted small-molecule synthesis

Some molecules are easy to draw on paper, whereas others contain rings and contortions that require one to think in three dimensions. Reisberg et al. set out to synthesize the bicyclic small molecule tryptorubin A but found that their initial attempt produced a molecule with the right bonds but the wrong molecular shape, a form of noncanonical atropisomerism. The authors then devised a synthesis where they locked in the correct isomer before forming the second ring, which produced a product indistinguishable from the authentic natural product. Such structural isomers may be lurking when working with complex small molecules with constrained rotation.

Science, this issue p. 458

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