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Synthesis

Biomimetic Route Delivers Epicolactone

Organic Synthesis: Study of biosynthetic pathway inspires unusually efficient synthesis of a fungal natural product

by Stu Borman
September 14, 2015 | APPEARED IN VOLUME 93, ISSUE 36

A study of the probable biosynthetic pathway leading to a recently isolated natural product has made it possible for researchers to achieve the first total synthesis of the compound in an unusually efficient manner (Nat. Chem. 2015, DOI: 10.1038/nchem.2336). The racemic natural product epicolactone was isolated from fungi about three years ago and found to have antimicrobial activity and, ironically, antifungal activity as well. Epicolactone’s three quaternary stereocenters, complex hydroxyl and keto functionalization, and polycyclic structure make it a challenging synthetic target. Dirk Trauner and coworkers at Ludwig Maximilian University of Munich met the challenge by going back to the source and figuring out how the natural product was most likely biosynthesized. Mimicking the biosynthetic route enabled them to assemble the structure in only eight steps from vanillyl alcohol. A key part of the synthesis is a cascade reaction that combines two aromatic starting materials into a caged compound with five rings, three quaternary carbons, and a tertiary alcohol. “It would be very difficult to design a cascade at this level of complexity from first principles,” the researchers write, showing that emulating nature can be a worthwhile synthetic strategy.

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