title: Total synthesis of (-)-2-epi-peloruside A.
abstract: A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).
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: Jason M
authors.initials: JM
authors.lastname: Cox
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Furuichi
authors.forename: Craig S
authors.initials: CS
authors.lastname: Kenesky
authors.forename: Junying
authors.initials: J
authors.lastname: Zheng
authors.forename: Onur
authors.initials: O
authors.lastname: Atasoylu
authors.forename: William M
authors.initials: WM
authors.lastname: Wuest
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds; D007783:Lactones; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C414085:peloruside A