title: One-pot Eschenmoser episulfide contractions in DMSO: applications to the synthesis of fuligocandins A and B and a number of vinylogous amides.
abstract: Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DMSO proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.
authors.affiliation: Unit of Organic Chemistry, Department of Biosciences at Novum, Karolinska Institute, SE-141 57 Huddinge, Sweden.
authors.forename: Birgitta
authors.initials: B
authors.lastname: Pettersson
authors.forename: Vedran
authors.initials: V
authors.lastname: Hasimbegovic
authors.forename: Jan
authors.initials: J
authors.lastname: Bergman
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013440:Sulfides / Q000737:chemistry*
chemical_list: D000577:Amides; D013440:Sulfides; C558766:fuligocandin A; C523500:fuligocandin B; D011392:Proline; D004121:Dimethyl Sulfoxide