Ab iomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical researchc ommunities.Aconcise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create alibrary of related compounds.Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOAderived meroterpenoid frameworks in six steps from commercially available starting materials.F urthermore,s everal farnesyl alkene substrates were used to generate structurally novel, DMOA-derived meroterpenoid derivatives.D FT calculations combined with experimentation provided ar ationale for the observed thermodynamic distribution of polycyclization products. Figure 1. a) RepresentativeDMOA-derived meroterpenoid natural products. b) Biosyntheses of the DMOA-derived meroterpenoids.
OpenBU http://open.bu.edu Chemistry BU Open Access Articles 2020-09-15 Exploiting the potential of meroterpenoid cyclases to expand the chemical space of fun...
OpenBU http://open.bu.edu Chemistry BU Open Access Articles 2020-09-15 Exploiting the potential of meroterpenoid cyclases to expand the chemical space of fun...
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