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.
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.
Tsujimori
H
H
Department of Chemistry, Faculty of Science, Science University of Tokyo, Japan.
Mori
K
K
D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D006801:Humans; D008848:Micromonosporaceae / Q000378:metabolism*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013879:Thioredoxins / Q000037:antagonists & inhibitors
C095251:BE 40644; D016227:Benzoquinones; D012717:Sesquiterpenes; D013879:Thioredoxins