Issue 3, 2000

Reductive thioalkylation of a pyranonaphthoquinone

Abstract

Reduction of pyranonaphthoquinone 6 with sodium dithionite in the presence of the sulfur nucleophiles thiocresol, phenylmethanethiol and butanethiol afforded the thioalkylated products 7 and 8, 9 and 10, and 11 and 12 respectively. This observed reductive thioalkylation at C-4 supports the postulate that naturally occurring pyranonaphthoquinone antibiotics may act as bioreductive alkylating agents.

Article information

Article type
Paper
Submitted
01 Nov 1999
Accepted
14 Nov 1999
First published
25 Jan 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 317-322

Reductive thioalkylation of a pyranonaphthoquinone

M. A. Brimble and M. R. Nairn, J. Chem. Soc., Perkin Trans. 1, 2000, 317 DOI: 10.1039/A908680C

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