title: 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 (CH₃)₃SiI 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.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. wrn0722@sina.com.
authors.forename: Ruina
authors.initials: R
authors.lastname: Wang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. liuguoyue001@126.com.
authors.forename: Guoyue
authors.initials: G
authors.lastname: Liu
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. yangmy@cau.edu.cn.
authors.forename: Mingyan
authors.initials: M
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. wangma@cau.edu.cn.
authors.forename: Mingan
authors.initials: M
authors.lastname: Wang
authors.affiliation: Department of Plant Pathology, China Agricultural University, Beijing 100193, China. lgzhou@cau.edu.cn.
authors.forename: Ligang
authors.initials: L
authors.lastname: Zhou
mesh_terms: D000215:Acylation; D000840:Anisoles / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D005658:Fungi / Q000187:drug effects; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000840:Anisoles; D000935:Antifungal Agents; D009281:Naphthalenes; D013141:Spiro Compounds; C060998:anisole
keywords: antifungal activities; ketalization; palmarumycin CP17; spirobisnaphthalene; total synthesis