Synthesis of the racemate of the stereoisomer at C-6a of BE-40644, a bioactive metabolite of Actinoplanes sp. with a sesquiterpene-substituted p-benzoquinone structure.

Article abstract of DOI:10.1271/bbb.65.167

BE-40644 is a tetracyclic metabolite of Actinoplanes sp. A 40644 possessing a sesquiterpene-substituted p-benzoquinone structure with cis-fused B/C ring stereochemistry that inhibits the human thioredoxin system as the well as the growth of several cancer cell lines. Its B/C trans-fused stereoisomer at C-6a was synthesized as a racemate starting from geranylacetone and 3,5-dihydroxybenzoic acid.

Full text of DOI:10.1271/bbb.65.167

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Bioscience, Biotechnology, and Biochemistry
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Synthesis of the Racemate of the Stereoisomer
at C-6a of BE-40644, a Bioactive Metabolite of
Actinoplanes sp. with a Sesquiterpene-substituted p-
Benzoquinone Structure
Hisayuki TSUJIMORIab & Kenji MORIa
a Department of Chemistry, Faculty of Science, Science University of Tokyo
b Research fellow on leave from Otsuka Pharmaceutical Co.
Published online: 22 May 2014.
To cite this article: Hisayuki TSUJIMORI & Kenji MORI (2001) Synthesis of the Racemate of the Stereoisomer at C-6a
of BE-40644, a Bioactive Metabolite of Actinoplanes sp. with a Sesquiterpene-substituted p-Benzoquinone Structure,
Bioscience, Biotechnology, and Biochemistry, 65:1, 167-171, DOI: 10.1271/bbb.65.167
To link to this article: http://dx.doi.org/10.1271/bbb.65.167
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