A Facile Total Synthesis of Neurotrophic Metabolite (+/-)-Neuchromenin

Josierika   A. Ferreira   Ramos; Tanus   J.   Nagem; Jason   G.   Taylor

doi:10.2174/15701786113106660088

Abstract

The synthesis of (+/-)-neuchromenin, a known natural product that induces neurite outgrowth of PC12 cells, is described. The total synthesis involved constructing a chromone ring from sesamol and coupling this intermediate to an aldehyde by a Morita-Baylis-Hillman reaction (MBH). The MBH adduct was cyclized under acidic conditions followed by removal of a methylene group to afford (+/-)-neuchromenin in 9 steps from sesamol.

Keywords: Neuchromenin, sesamol, fries rearrangement, Baylis-Hillman Reaction.

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Letters in Organic Chemistry

Title:A Facile Total Synthesis of Neurotrophic Metabolite (+/-)-Neuchromenin

Volume: 11 Issue: 3

Author(s): Josierika A. Ferreira Ramos, Tanus J. Nagem and Jason G. Taylor

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Keywords: Neuchromenin, sesamol, fries rearrangement, Baylis-Hillman Reaction.

Abstract: The synthesis of (+/-)-neuchromenin, a known natural product that induces neurite outgrowth of PC12 cells, is described. The total synthesis involved constructing a chromone ring from sesamol and coupling this intermediate to an aldehyde by a Morita-Baylis-Hillman reaction (MBH). The MBH adduct was cyclized under acidic conditions followed by removal of a methylene group to afford (+/-)-neuchromenin in 9 steps from sesamol.

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Ramos A. Ferreira Josierika, Nagem J. Tanus and Taylor G. Jason, A Facile Total Synthesis of Neurotrophic Metabolite (+/-)-Neuchromenin, Letters in Organic Chemistry 2014; 11 (3) . https://dx.doi.org/10.2174/15701786113106660088