title: Room-temperature B(OAc)3-promoted Diels-Alder reaction of juglone with styrenes: total syntheses of tetrangulol and anhydrolandomycinone.
abstract: The Diels-Alder reaction of juglone with various styrenes in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) was promoted by B(OAc)(3) at room temperature. The reaction proceeded smoothly and gave the products in a good yield and with excellent regioselectivity. This strategy was applied to the total syntheses of tetrangulol and anhydrolandomycinone.
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University, Minhsiung, Taiwan 621. chedsh@ccu.edu.tw
authors.forename: Day-Shin
authors.initials: DS
authors.lastname: Hsu
authors.forename: Jiun-Yi
authors.initials: JY
authors.lastname: Huang
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*; D013696:Temperature
chemical_list: D001896:Boron Compounds; D009285:Naphthoquinones; D009844:Oligosaccharides; D013343:Styrenes; C490012:anhydrolandomycinone; C005134:juglone