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Total Synthesis of (±)-Illisimonin A, a Neuroprotective Sesquiterpenoid from the Fruits of Illicium simonsii

preprint
submitted on 14.06.2019 and posted on 17.06.2019 by Alexander S. Burns, Scott Rychnovsky

Illisimonin A was isolated from Illicium simonsii and has a previously unreported tricyclic carbon framework. It displayed neuroprotective effects against oxygen-glucose deprivation-induced cell injury in SH-SY5Y cells. It incorporates a highly strained trans-pentalene ring system. We report the first synthesis of illisimonin A. Notable steps in the route include a 1,3-dioxa-2-silacyclohexenetemplated Diels-Alder cycloaddition and type-3 semipinacol rearrangement to generate the trans-pentalene. The final step is an iron-catalyzed C-H oxidation. The synthetic route is robust, with 94 mg prepared in a single pass.

Funding

uc Irvine

History

Email Address of Submitting Author

srychnov@uci.edu

Institution

UC Irvine

Country

USA

ORCID For Submitting Author

0000-0002-7223-4389

Declaration of Conflict of Interest

no conflict of interest

Version Notes

June 6 2019 draft

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