Synthesis 2018; 50(19): 3931-3935
DOI: 10.1055/s-0036-1591587
paper
© Georg Thieme Verlag Stuttgart · New York

A Simple Route to Benzo[b]xanthene-6,11,12-triones: Synthesis of Bikaverin

Dmitry N. Pelageev
a   G. B. Elaykov Pacific Institute of Bioorganic Chemistry, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Email: anufriev@piboc.dvo.ru
b   School of Natural Sciences, Far Eastern Federal University, Sukhanova St. 8, 690950 Vladivostok, Russian Federation
,
Ksenia L. Borisova
a   G. B. Elaykov Pacific Institute of Bioorganic Chemistry, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Email: anufriev@piboc.dvo.ru
,
Victor Ph. Anufriev*
a   G. B. Elaykov Pacific Institute of Bioorganic Chemistry, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Email: anufriev@piboc.dvo.ru
› Author Affiliations
Further Information

Publication History

Received: 23 April 2018

Accepted after revision: 24 April 2018

Publication Date:
09 July 2018 (online)


Abstract

A three-step procedure for the synthesis of 1H-benzo[b]xanthene-6,11,12-trione derivatives is described. The procedure involves the halogenation of 12-(3-hydroxy-1,4-naphthoquinon-2-yl)-6H-benzo[b]xanthene-6,11-(12H)-diones, followed by treatment with water under aeration. In this manner, bikaverin, a cytotoxic metabolite isolated from several species of the fungal genera Gibberella, Fusarium, and Mycogone, was synthesised.

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