title: Divergent synthesis of cytotoxic styryl lactones related to goniobutenolides A and B, and to crassalactone D.
abstract: Goniobutenolides A (1) and B (2), crassalactone D (3), 4-epi-crassalactone D (4), and the corresponding 7-epimers have been synthesized starting from d-glucose. The key step in the synthesis of 1 and 2 is a new one-pot sequence comprised of a Z-selective Wittig olefination/lactonization/β-elimination. Preparation of 3 and 4 included the final 5-endo-trig spirocyclization of 1 and 2. The synthesized products were evaluated for their in vitro antiproliferative activity against selected tumor cell lines.
authors.affiliation: Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 3, 21000 Novi Sad, Serbia. velimir.popsavin@dh.uns.ac.rs
authors.forename: Velimir
authors.initials: V
authors.lastname: Popsavin
authors.forename: Ivana
authors.initials: I
authors.lastname: Kovačević
authors.forename: Goran
authors.initials: G
authors.lastname: Benedeković
authors.forename: Mirjana
authors.initials: M
authors.lastname: Popsavin
authors.forename: Vesna
authors.initials: V
authors.lastname: Kojić
authors.forename: Gordana
authors.initials: G
authors.lastname: Bogdanović
mesh_terms: D029061:Annonaceae / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005947:Glucose / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D020014:K562 Cells; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; D013141:Spiro Compounds; C545739:crassalactone D; C578361:goniobutenolide A; C578362:goniobutenolide B; D005947:Glucose