title: Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis.
abstract: We report a new method for constructing the ABC ring system of strigolactones, in a single step from a simple linear precursor by acid-catalyzed double cyclization. The reaction proceeds with a high degree of stereochemical control, which can be qualitatively rationalized using DFT calculations. Our concise synthetic approach offers a new model for thinking about the (as yet) unknown chemistry that is employed in the biosynthetic pathways leading to this class of plant hormones.
authors.affiliation: Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, USA.
authors.forename: Kinga
authors.initials: K
authors.lastname: Chojnacka
authors.forename: Stefano
authors.initials: S
authors.lastname: Santoro
authors.forename: Radi
authors.initials: R
authors.lastname: Awartani
authors.forename: Nigel G J
authors.initials: NG
authors.lastname: Richards
authors.forename: Fahmi
authors.initials: F
authors.lastname: Himo
authors.forename: Aaron
authors.initials: A
authors.lastname: Aponick
mesh_terms: D002412:Cations / Q000737:chemistry; D003500:Cyclization; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010937:Plant Growth Regulators / Q000138:chemical synthesis / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: C524823:(4-hydroxy-5,8-dimethyl-3-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-3a,4-dihydro-3H-indeno(1,2-b)furan-2(8bH)-one; D002412:Cations; D007783:Lactones; D010937:Plant Growth Regulators; C483518:strigol