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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 11 , Issue 3 , 2014

Page: [194 - 196] Pages: 3

DOI: 10.2174/15701786113106660088

Price: $65


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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