title: Total synthesis of macrosphelides A, B, and E: first application of ring-closing metathesis for macrosphelide synthesis.
abstract: A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Takanori
authors.initials: T
authors.lastname: Kawaguchi
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Funamori
authors.forename: Yuji
authors.initials: Y
authors.lastname: Matsuya
authors.forename: Hideo
authors.initials: H
authors.lastname: Nemoto
mesh_terms: D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D006571:Heterocyclic Compounds; D018942:Macrolides; C097798:macrosphelide A; C097799:macrosphelide B; C483571:macrosphelide E