title: Total synthesis of (±)-epithuriferic acid methyl ester via Diels-Alder reaction.
abstract: In this paper, we have described the first total synthesis of (±)-epithuriferic acid methyl ester from non-natural sources, in four steps (20% overall yield). The key step involves the Diels-Alder reaction of isobenzofuran with methyl 3-(dimethoxyphosphoryl)acrylate which is controlled by "ortho" regio- and endo stereoselectivities due to the COOMe group.
authors.affiliation: Department of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, Łódź, 9-363 Poland. mkopr@cbmm.lodz.pl.
authors.forename: Marek
authors.initials: M
authors.lastname: Koprowski
authors.affiliation: Department of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, Łódź, 9-363 Poland. mkopr@cbmm.lodz.pl and Jan Długosz University in Częstochowa, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Armii Krajowej 13/15, Częstochowa, 42-201, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Bałczewski
authors.affiliation: Department of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, Łódź, 9-363 Poland. mkopr@cbmm.lodz.pl.
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Owsianik
authors.affiliation: Jan Długosz University in Częstochowa, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Armii Krajowej 13/15, Częstochowa, 42-201, Poland.
authors.forename: Ewa
authors.initials: E
authors.lastname: Różycka-Sokołowska
authors.affiliation: Jan Długosz University in Częstochowa, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Armii Krajowej 13/15, Częstochowa, 42-201, Poland.
authors.forename: Bernard
authors.initials: B
authors.lastname: Marciniak
mesh_terms: D001572:Benzofurans / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D002227:Carbazoles; D009281:Naphthalenes; C000611559:epithuriferic acid methyl ester