title: Asymmetric synthesis of (+)-galbelgin, (-)-kadangustin J, (-)-cyclogalgravin and (-)-pycnanthulignenes A and B, three structurally distinct lignan classes, using a common chiral precursor.
abstract: The enantioselective synthesis of three structurally distinct classes of lignan from a single, aza-Claisen-derived, chiral morpholine amide is reported. The class of lignan formed is dependent on the substitution pattern in the aryl rings and choice of protecting group on a key benzylic hydroxyl group. The methodology has been used to asymmetrically synthesize and determine the absolute stereochemistry of lignans (+)-cyclogalgravin 3, (-)-pycnanthulignene A 4, (-)-pycnanthulignene B 5, and (-)-kadangustin J 8.
authors: School of Chemical Sciences, University of Auckland, Auckland, New Zealand.
authors: Claire E
authors: CE
authors: Rye
authors: David
authors: D
authors: Barker
mesh_terms: D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005663:Furans; D017705:Lignans; C568372:kadangustin J; C548108:pycnanthulignene A; C568373:pycnanthulignene B; C084077:galgravin