A pinboard by Marie Isabel Thomson

Chemistry PhD Student, The University of Edinburgh, Lawrence Group

Pinboard Summary

(+)-Angiopterlactone B is a structurally complex bis-lactone metabolite, which was isolated from the rhizome of Angiopteris caudatiformis by Zou and co-workers in 2009. The structural complexity of this metabolite, as well as the biological activities reported for the extracts of Angiopteris plants, make this compound of significant interest to synthetic chemists.

Synthetic biomimetic investigations have successfully resulted in a four-step total synthesis of (−)-angiopterlactone B, starting from commercially available 2-acetylfuran. The structure, including absolute stereochemistry, was confirmed by X-ray crystallography. Particularly noteworthy is the final biomimetic dimerisation, which forms three new bonds, two new rings and three new contiguous stereogenic centres in a single step. This synthesis exemplifies how biosynthetic considerations can lead to the development of domino reaction sequences, which rapidly generate molecular complexity.

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