title: An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.
abstract: Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States.
authors.forename: Sudeshna
authors.initials: S
authors.lastname: Roy
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Spilling
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D000459:Phaeophyceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D005663:Furans; D008055:Lipids; D010165:Palladium