title: Bioinspired total synthesis of gymnothelignan N.
abstract: Bioinspired total synthesis of gymnothelignan N was accomplished in 13 steps and 6.7% overall yield. The synthesis features a syn Evans aldol reaction, an intramolecular hydrogenative dehydration reaction, and a phenol oxidative dearomatization/Friedel-Crafts reaction, which provides a new plausible biosynthetic pathway for the gymnothelignans and other symbiotic members. Meanwhile, another tetrahydrofuran-type lignan beilschmin A was also synthesized.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University , Lanzhou 730000, People's Republic of China.
authors.forename: Huilin
authors.initials: H
authors.lastname: Li
authors.forename: Yuanyuan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Xingang
authors.initials: X
authors.lastname: Xie
authors.forename: Haichen
authors.initials: H
authors.lastname: Ma
authors.forename: Changgui
authors.initials: C
authors.lastname: Zhao
authors.forename: Gaoyuan
authors.initials: G
authors.lastname: Zhao
authors.forename: Xuegong
authors.initials: X
authors.lastname: She
mesh_terms: D000447:Aldehydes; D005663:Furans; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D032134:Saururaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D005663:Furans; D017705:Lignans; C000598264:beilschmin A; C000598263:gymnothelignan N; C018674:tetrahydrofuran; C116609:3-hydroxybutanal