Total Syntheses of Aurachins A and B. (4th May 2017)

• Record Type: Journal Article
• Authors: Hattori, Haruhiko; Yokoshima, Satoshi; Fukuyama, Tohru
• Is Part Of: Angewandte Chemie. Volume 129:Number 24(2017)
• Page Start: 7084
• Page End: 7087
• Publication Date: 2017-05-04
• Subjects: Alkaloide -- Cyclisierungen -- Naturstoffe -- N-Oxide -- Totalsynthesen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201702204
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.