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

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

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 3 , 2014

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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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Article Details

VOLUME: 11
ISSUE: 3
Year: 2014
Page: [194 - 196]
Pages: 3
DOI: 10.2174/15701786113106660088
Price: $65

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