A new polyphenolic compound formed during maple syrup processing from acer saccharum’s sap, quebecol, has been recently reported1. Its structural similarity with common bioactive agents and its potential bioactive and antioxidant properties lead our group to work on the total synthesis of quebecol. Our synthetic approach involves two key steps. The first one consists of a C-1 Wittig type homogation reaction, a Ramirez olefination, on an α-ketoester to produce a dibromoalkene analog. This product is used in the second key step: a double Suzuki-Miyaura cross-coupling with the appropriate arylboronic acid using conditions optimised for hindered systems. This efficient and convenient strategy has led us to prepare quebecol on a large scale2. Moreover, this convergent synthetic route allowed us to prepare a series of analogs of quebecol. In this presentation, we will present the synthesis of quebecol and its analogs, as well as their anti-inflammatory activity.

Synthesis and characterization of the bioactivity of quebecol and its analogs

253rd National Meeting (2017)

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