title: Transmissive olefination route to putative "morinol I" lignans.
abstract: A series of morinol-type lignans were rapidly assembled using a Grignard-based transmissive olefination. In combination with palladium-catalyzed arylations, the strategy provides stereoselective access to (7Z,7'E), (7E,7'E), and (7E,7'Z) morinol diastereomers and the (7Z,8'E) and (7E,8'E) conjugated analogues. Critical for the E/Z stereoselectivity is a new, general method for converting alkenenitriles to alkenemethanols that circumvents the enal E/Z isomerization commonly encountered during conventional i-Bu(2)AlH reduction.
authors.affiliation: Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA.
authors.forename: Lihua
authors.initials: L
authors.lastname: Yao
authors.forename: Bhaskar
authors.initials: B
authors.lastname: Pitta
authors.forename: P C
authors.initials: PC
authors.lastname: Ravikumar
authors.forename: Matthew
authors.initials: M
authors.lastname: Purzycki
authors.forename: Fraser F
authors.initials: FF
authors.lastname: Fleming
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D017705:Lignans / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D017705:Lignans; D010165:Palladium