title: Biomimetic total synthesis of (+)-himbacine.
abstract: On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensation followed by an iminium ion activated intramolecular Diels-Alder cycloaddition to give the (+)-himbacine precursor 11 on reductive work up. Compound 11 was converted into (+)-himbacine in four synthetic steps. [reaction: see text]
authors.affiliation: Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, United Kingdom.
authors.forename: Kirill
authors.initials: K
authors.lastname: Tchabanenko
authors.forename: Robert M
authors.initials: RM
authors.lastname: Adlington
authors.forename: Andrew R
authors.initials: AR
authors.lastname: Cowley
authors.forename: Jack E
authors.initials: JE
authors.lastname: Baldwin
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000447:Aldehydes; D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes; D005663:Furans / Q000138:chemical synthesis*; D008958:Models, Molecular; D009281:Naphthalenes / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D000475:Alkenes; D005663:Furans; D009281:Naphthalenes; D010880:Piperidines; C004511:butenolide; D014269:Trifluoroacetic Acid; C048172:himbacine; D015107:4-Butyrolactone