title: Asymmetric synthesis of (-)-martinellic acid.
abstract: A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3-[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant β-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, UK. steve.davies@chem.ox.ac.uk
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: Ai M
authors.initials: AM
authors.lastname: Fletcher
authors.forename: James A
authors.initials: JA
authors.lastname: Lee
authors.forename: Thomas J A
authors.initials: TJ
authors.lastname: Lorkin
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry; D018360:Crystallography, X-Ray; D004952:Esters; D008094:Lithium / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D000577:Amides; D004952:Esters; D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid; D008094:Lithium; D014269:Trifluoroacetic Acid