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Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues.

ABSTRACT: Total synthesis of naturally occurring spirobisnaphthalene palmarumycin CP17 and its methoxy analogues was first achieved through Friedel-Crafts acylation, Wolff-Kishner reduction, intramolecular cyclization, ketalization, benzylic oxidation, and demethylation using the inexpensive and readily available methoxybenzene, 1,2-dimethoxybenzene and 1,4-dimethoxybenzene and 1,8-dihydroxynaphthalene as raw materials. Demethylation with (CH?)?SiI at ambient temperature resulted in ring A aromatization and acetal cleavage to give rise to binaphthyl ethers. The antifungal activities of these spirobisnaphthalene derivatives were evaluated, and the results revealed that 5 and 9b exhibit EC50 values of 9.34 µg/mL and 12.35 µg/mL, respectively, against P. piricola.

SUBMITTER: Wang R

PROVIDER: S-EPMC6274023 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues.

Wang Ruina R Liu Guoyue G Yang Mingyan M Wang Mingan M Zhou Ligang L

Molecules (Basel, Switzerland) 20160507 5

Total synthesis of naturally occurring spirobisnaphthalene palmarumycin CP17 and its methoxy analogues was first achieved through Friedel-Crafts acylation, Wolff-Kishner reduction, intramolecular cyclization, ketalization, benzylic oxidation, and demethylation using the inexpensive and readily available methoxybenzene, 1,2-dimethoxybenzene and 1,4-dimethoxybenzene and 1,8-dihydroxynaphthalene as raw materials. Demethylation with (CH₃)₃SiI at ambient temperature resulted in ring A aromatization a ...[more]

PMID: 27164077

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