Synthesis 2014; 46(20): 2763-2770
DOI: 10.1055/s-0034-1378522
paper
© Georg Thieme Verlag Stuttgart · New York

A New Method for Thiomethylation of Hydroxy-1,4-naphthoquinones with N-Acetyl-l-cysteine; First Synthesis of Fibrostatins B, C, and D

Yuri E. Sabutskii
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   eMail: sergpol@piboc.dvo.ru
,
Sergey G. Polonik*
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   eMail: sergpol@piboc.dvo.ru
,
Vladimir A. Denisenko
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   eMail: sergpol@piboc.dvo.ru
,
Pavel S. Dmitrenok
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   eMail: sergpol@piboc.dvo.ru
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Publikationsverlauf

Received: 21. April 2014

Accepted after revision: 24. Juni 2014

Publikationsdatum:
30. Juli 2014 (online)


Abstract

A series of N-acetyl-S-[(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl]-l-cysteine conjugates were obtained in good yields by acid-catalyzed condensation of substituted 2-hydroxy-1,4-naphthoquinones with N-acetyl-l-cysteine and paraform­aldehyde. Based on this reaction, a first synthesis of fibrostatins B, C, and D was developed.

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