title: (+)-Rimocidin synthetic studies. Construction of an advanced C(1-18) polyol fragment.
abstract: [structure: see text] The synthesis of an appropriately functionalized advanced C(1-18) polyol fragment of the mycosamine-glycosylated polyene macrolide, (+)-rimocidin (1), has been achieved in a highly efficient manner. Highlights of the strategy include the S(N)2/S(N)2' addition of dithiane anions to vinyl epoxides and the multicomponent linchpin union of 2-TBS-1,3-dithiane with two advanced epoxides.
authors.affiliation: Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: Suresh M
authors.initials: SM
authors.lastname: Pitram
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Fuertes
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry*; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
chemical_list: D000470:Alkaloids; D004852:Epoxy Compounds; D011090:Polyenes; D011108:Polymers; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C024617:polyol; C003273:rimocidin