Journal Article Total Syntheses of Aurachins A and B

Hattori, Haruhiko  ,  Yokoshima, Satoshi  ,  Fukuyama, Tohru

56 ( 24 )  , pp.6980 - 6983 , 2017-06-06 , Wiley
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.

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