title: Synthesis of bioactive speciosins G and P from Hexagonia speciosa.
abstract: The first total synthesis of speciosins P and G, previously isolated from Hexagonia speciosa, is reported. These compounds have been synthesized by Sonogashira coupling from readily available starting materials. Siccayne was also synthesized from the same starting material in two steps along with a number of other derivatives. The compounds were tested in the wheat coleoptile bioassay. The most active compound was the intermediate 18, followed by 29 and 17. The structural requirements for activity in these compounds are the presence of methoxy groups in the aromatic ring and a formyl or hydroxy group in the side chain.
authors.affiliation: Allelopathy Group, Department of Organic Chemistry, School of Sciences, INBIO Institute of Biomolecules, University of Cadiz , C/ República Saharaui, s/n, 11510-Puerto Real, Cádiz, Spain.
authors.forename: Guillermo A
authors.initials: GA
authors.lastname: Guerrero-Vásquez
authors.forename: Nuria
authors.initials: N
authors.lastname: Chinchilla
authors.forename: José M G
authors.initials: JM
authors.lastname: Molinillo
authors.forename: Francisco A
authors.initials: FA
authors.lastname: Macías
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001681:Biological Assay; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011124:Polyporaceae / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014908:Triticum / Q000187:drug effects / Q000254:growth & development
chemical_list: D000480:Alkynes; C000594560:speciosin G; C000594559:speciosin P; C031784:siccayne