title: Ketyl radical cyclization of β-disubstituted acrylates: formal syntheses of (+)-secosyrin 1 and longianone and the total synthesis of (+)-4-epi-secosyrin 1.
abstract: A novel approach to the synthesis of a series of 1,7-dioxaspirononanes that applies a ketyl radical cyclization strategy is described. Radical cyclization of the β-disubstituted acrylate 23, prepared in five steps from (R)-1,2-isopropylideneglycerol, gives both 2,3-syn- and 2,3-anti-furan products. The densely functionalized furan heterocycles are used to complete a concise formal synthesis of secosyrin 1, a metabolite of Pseudomonas syringae, and the total synthesis of 4-epi-secosyrin 1.
authors: Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010, Australia. cdonner@unimelb.edu.au
authors: Christopher D
authors: CD
authors: Donner
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D044224:Pseudomonas syringae / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C582265:4-epi-secosyrin 1; D000179:Acrylates; D005663:Furans; D007783:Lactones; D013141:Spiro Compounds; C552376:longianone; C489176:secosyrin 1