title: Enantioselective Synthesis of a Furan Lignan (+)-Sylvone.
abstract: A synthesis of natural tetrahydrofuran lignan (+)-sylvone is achieved starting from methyl allenoate in 5 steps. The synthesis begins from an enantioselective aldol reaction of methyl allenoate with 3,4-dimethoxybenzaldehyde to afford α-addition aldol adduct. Key steps for the synthesis of sylvone include an oxacyclization of the α-hydroxy allenyl adduct followed by a Michael addition of a 1,3-dithiane derivative to establish a sylvone skeleton with suitable stereoselections.
authors.affiliation: Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
authors.forename: Eunhye
authors.initials: E
authors.lastname: Lee
authors.affiliation: Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
authors.forename: Jiyun
authors.initials: J
authors.lastname: Bang
authors.affiliation: Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
authors.forename: Jisook
authors.initials: J
authors.lastname: Kwon
authors.affiliation: Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
authors.forename: Chan-Mo
authors.initials: CM
authors.lastname: Yu
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001547:Benzaldehydes; D005663:Furans; D006571:Heterocyclic Compounds; D017705:Lignans; D009281:Naphthalenes; C018674:tetrahydrofuran; C012947:1,3-dithiane; C110055:allenolic acid; C427725:veratraldehyde