title: Synthesis of (-)-neothiobinupharidine.
abstract: An eight step, asymmetric synthesis of a dimeric thiaspirane nuphar alkaloid from 3-methyl-2-cyclo-pentenone is reported. The brevity of the route relies on a useful procedure for tandem reductive allylation of cyclopentenones, as well as the minimization of redox manipulations and other functional group interconversions. The distribution of products that arise from spontaneous dimerization points to a more complex biosynthesis.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Jansen
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Shenvi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D005663:Furans; D013141:Spiro Compounds; C582349:neothiobinupharidine