Synthesis of Gerfelin and Related Analogous Compounds

Md. Sadequl ISLAM; Mitsuhiro KITAGAWA; Masaya IMOTO; Takeshi KITAHARA; Hidenori WATANABE

doi:10.1271/bbb.60287

This article has now been updated. Please use the final version.

Synthesis of Gerfelin and Related Analogous Compounds

Md. Sadequl ISLAM, Mitsuhiro KITAGAWA, Masaya IMOTO, Takeshi KITAHARA, Hidenori WATANABE

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Keywords: gerfelin, geranylgeranyl diphosphate synthase, enzyme inhibitor

JOURNAL FREE ACCESS Advance online publication

Article ID: 60287

DOI https://doi.org/10.1271/bbb.60287

The final version of this article is now available: Vol. 70 (2006) , No. 10 p.2523

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Abstract

Gerfelin, an inhibitor of human geranylgeranyl diphosphate (GGPP) synthase that has been isolated from a culture broth of Beauveria felina QN22047, was synthesized in 4 and 3 steps starting from 2,4-dihydroxy-6-methylbenzoic acid and 3,4,5-trihydroxytoluene, respectively. An effective ligand, 2-(di-tert-butylphosphino)biphenyl, was used in the palladium-catalyzed diaryl ether-forming reaction. Five analogous compounds of gerfelin were also synthesized for a study of the structure-activity relationship.

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