title: Synthesis, reactions and structure-activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: illudin analogs with in vitro cytotoxic activity.
abstract: 1-Hydroxyspiro[2.5]cyclooct-4-en-3-ones-analogs of natural illudines--were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro[2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied.
authors.affiliation: Institut für Chemie und Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany.
authors.forename: Gopal
authors.initials: G
authors.lastname: Bose
authors.forename: Karin
authors.initials: K
authors.lastname: Bracht
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Bednarski
authors.forename: Michael
authors.initials: M
authors.lastname: Lalk
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D018922:HL-60 Cells; D006801:Humans; D066298:In Vitro Techniques; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013141:Spiro Compounds; C052673:illudin M