Synthesis of a new microbial secondary metabolite: anti-Helicobacter pylori CJ-13,015 |
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Authors: | Mukulesh Mondal |
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Affiliation: | Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India |
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Abstract: | A six-step, first synthesis of an anti-Helicobacter pylori secondary metabolite, CJ-13,015 (1a), in 65% overall yield, is described, starting from 5-methylfurfural (2), via a Wittig reaction of the ylide generated in situ from (8-hydroxyoctyl)triphenylphosphonium bromide, selective reduction of the newly formed carbon-carbon double bond, conversion of the alcohol to a halide, coupling with the anion of 3,5-dimethoxyphthalide and a chemoselective conversion of the protective furan group to a 1,4-dicarbonyl system as a key reaction. |
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Keywords: | Microbial secondary metabolite CJ-13,015 anti-Helicobacter pylori 5-Methylfurfural Coupling reactions Furan to 1,4-dicarbonyl system Total synthesis |
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