4 years ago

Total Syntheses of Aurachins A and B

Total Syntheses of Aurachins A and B
Satoshi Yokoshima, Tohru Fukuyama, Haruhiko Hattori
Aurachins A and B are alkaloids having 3-hydroxyquinoline N-oxide cores. An efficient method for the synthesis of 3-hydroxyquinoline N-oxides was established and is amenable to the total syntheses of aurachins A and B. Alkylation of 1-(2-nitrophenyl)butan-2-one with farnesyl bromide took place selectively at the benzylic position, and subsequent treatment of the alkylated product with sodium tert-butoxide in dimethyl sulfoxide gave aurachin B. Alkylation of 1-(2-nitrophenyl)butan-2-one with an epoxy iodide derived from farnesol was used to access aurachin A. The total syntheses of the title compounds were achieved by employing a NaH-mediated cyclization protocol. Reactions of 1-(2-nitrophenyl)butan-2-one with an epoxy iodide, which was derived from farnesol, in the presence of NaH induced selective alkylation at the benzylic position and subsequent cyclization to produce aurachin A.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702204

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