title: Phosphate tethers in natural product synthesis.
abstract: Recent advances in phosphate tether-mediated natural product synthesis are reviewed. Synthetic approaches toward dolabelide C, (-)-salicylihalimide A, (-)-tetrahydrolipstatin, and (+)-strictifolione are included. In addition, current efforts in method development are briefly reviewed, including a detailed study on the effect of stereochemical complexity on the phosphate-mediated, diastereoselective ring-closing metathesis reaction and recent advances in multi-reaction, one-pot sequential processes mediated by the phosphate tether. Overall, this review seeks to highlight the utility of phosphate triesters to serve as multifunctional tethers with protecting group and latent leaving group characteristics and the ability to orchestrate multiple, orthogonal reaction pathways to allow for the facile synthesis of complex, bioactive small molecules and their analogs.
authors.affiliation: Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., 2010 Malott Hall, Lawrence, KS, 66045-7572, USA, phanson@ku.edu.
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
authors.forename: Susanthi
authors.initials: S
authors.lastname: Jayasinghe
authors.forename: Soma
authors.initials: S
authors.lastname: Maitra
authors.forename: Jana L
authors.initials: JL
authors.lastname: Markley
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure; D000077403:Orlistat; D010710:Phosphates / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; D018942:Macrolides; D010710:Phosphates; D011753:Pyrones; C524147:dolabelide C; C410986:salicylihalamide A; C476921:strictifolione; D000077403:Orlistat