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Synlett 2011(11): 1551-1554  
DOI: 10.1055/s-0030-1260771
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Method to Prepare 3-Alkyl-2-hydroxy-1,4-naphthoquinones:
Synthesis of Lapachol and Phthiocol

Sabrina Baptista Ferreiraa, David Rodrigues da Rochab, José Walkimar M. Carneiroc, Wilson Costa Santosd, Vitor Francisco Ferreira*b
a Universidade Federal do Rio de Janeiro, Instituto de Química, 27930-560 Macáe, Rio de Janeiro, Brazil
b Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, 24020-141 Niterói, Rio de Janeiro, Brazil
Fax: +55(21)26292362; e-Mail: cegvito@vm.uff.br;
c Universidade Federal Fluminense, Instituto de Química, Departamento de Química Inorgânica, 24020-141 Niterói, Rio de Janeiro, Brazil
d Universidade Federal Fluminense, Faculdade de Farmácia, Departamento de Farmácia e Administração Farmacêutica, 24241-000 Niterói, Rio de Janeiro, Brazil
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Publikationsverlauf

Received 24 January 2011
Publikationsdatum:
10. Juni 2011 (online)

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Abstract

In this article a mild, simple, safe, and chemoselective synthesis and reduction of o-quinone methides to the corresponding 3-alkyl-2-hydroxy-1,4-naphthoquinones, compounds with interesting biological activity, mediated by the formic acid-water system is described. This new one-pot methodology was applied to the synthesis of lapachol and constitutes an efficient and inexpensive alternative for the preparation of this natural bioactive compound

Key words

reduction - quinones - alkylation - lapachol - phthiocol