The five-step synthesis of the new 4H-anthra[1,2-b]pyran derivative 1 is reported. The key steps in this approach included a Marschalk alkylation of 1,4-dihydroxyanthraquinone followed by a Baker–Venkataraman reaction and then an acid-catalyzed cyclization of ring A to form the 4H-anthra[1,2-b]pyran system. Two compounds, the 4H-anthra[1,2-b]pyran 1 and the anthraquinone derivative 6 were evaluated for antimicrobial activity and showed moderate antialgal, antifungal, and antibacterial activities.
SéquinU. (1986) The Antibiotics of the Pluramycine Group (4 H-Anthra[1,2-b]pyran Antibiotics). Progress Chemistry Organic Natural Products, Vol.50, 58–122; (b) Hansen MR, Hurley LH (1996) Pluramycins. Old Drugs Having Modern Friends in Structural Biology. Accounts Chemical Research29, 249-258.
2.
LomboF., KünzelE., PradoL., BranaA.F., BindseilK.U., FrevertJ., BeardenJ., MendezC., Sala'sJ., RohrJ. (2000) The novel hybrid antitumor compound premithramycinone H provides indirect evidence for a tricyclic intermediate of the biosynthesis of the aureolic acid antibiotic mithramycin. Angewandte Chemie International Edition, 39, 796–799; (b) Krohn K, Vitz J. (2004) Total synthesis of premithramycinone H and related anthrapyran antibiotics. European Journal Organic Chemistry, 209-219.
3.
KanaiY., IshiyamaD., SendaH., IwataniW., TakahashiH., KonnoH., TokumasuS., KanazawaS. (2000) Novel Human Topoisomerase I Inhibitors, Topopyrones A, B, C, and D. Part 1. Producing Strain, Fermentation, Isolation, Physicochemical Properties and Biological Activity. Journal of Antibiotics, 53, 863–872; (b) Dallavalle S, Gattinoni S, Mazzini S, Scaglioni L, Merlini L, Tinelli S, Beretta GL, Zunino F (2008) Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors. Bioorganic Medicinal Chemistry Letters, 18, 1484–1489.
4.
KimJ.S., Shin-YaK., EishimaJ., FurihataK., SetoH. (1996) A novel neuronal cell protecting substance, espicufolin, produced by Streptomyces sp. Journal of Antibiotics, 49, 947–948.
5.
KrohnK., HemmeC. (1979) Synthetische Anthracyclinone, VI. Synthese strukturanaloger Anthracyclinone. Liebigs Annalen der Chemie, 35–42; (b) Krohn K, Hemme C (1979) Synthetische Anthracyclinone, V. Alkylierung von Anthrachinonen als variabler Syntheseweg zu Anthracyclinon-Vorstufen. Liebigs Annalen der Chemie, 19-34.
6.
MarschalkC., KoenigF., OuroussoffN. (1936) Nouvelle méthode d'introduction des chaines latérales dans le noyau anthraquinoique. Bulletin Societé Chimique France, 3, 1545–1575.
7.
KrohnK., RoemerE., TopM. (1996) Total synthesis of Aklanonic Acid and Derivatives by Baker-Venkataraman Rearrangement. Liebigs Annalen, 271–277.
8.
KrohnK., GehleD., KampO., van ReeT. (2003) Highly deoxygenated Sugars. II. Synthesis of chiral cyclopentenes via novel carbocyclization of C-4 branched deoxysugars. Journal of Carbohydrate Chemistry, 22, 377–383.