A Biomimetic Synthesis of des-Hydroxy Paecilospirone

A Biomimetic Synthesis of des-Hydroxy Paecilospirone: Z.-G. Feng, G. L. Burnett, T. R. R. Pettus
Synlett 2018, DOI: 10.1055/s-0036-1592001

Paecilospirone is a spiro[chroman-2,1′(3′H)-isobenzofuran], first collected from the marine fungus Paecilomyces sp. near Yap Island, that was reported to inhibit microtubule assembly. A total synthesis of (+)-paecilospirone in 19 steps was reported in 2011. Recently, the group of Professor Thomas R. R. Pettus from University of California (Santa Barbara, USA) reported a new bio-inspired approach to the title compound. The synthesis is de facto based on the dimerization of a single precursor molecule derived from 3-hydroxybenzoic acid.

Professor Pettus said: “Recognizing advancements in organic chemistry is impossible without natural product syntheses serving in the role of a definitive yardstick. Those methods and strategies, that are the most emulative of nature, will usually prove to be the more useful and efficient, and continue to demonstrate their utility well into the future.”
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