title: Facile access to cis-2,6-disubstituted tetrahydropyrans by palladium-catalyzed decarboxylative allylation: total syntheses of (±)-centrolobine and (+)-decytospolides A and B.
abstract: cis-2,6-Tetrahydropyran is an important structural skeleton of bioactive natural products. A facile synthesis of cis-2,6-disubstituted-3,6-dihydropyrans as cis-2,6-tetrahydropyran precursors has been achieved in high regio- and stereoselectivity with high yields. This reaction involves a palladium-catalyzed decarboxylative allylation of various 3,4-dihydro-2H-pyran substrates. Extending this reaction to 1,2-unsaturated carbohydrates allowed the achievement of challenging β-C-glycosylation. Based on this methodology, the total syntheses of (±)-centrolobine and (+)-decytospolides A and B were achieved in concise steps and overall high yields.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
authors.forename: Jing
authors.initials: J
authors.lastname: Zeng
authors.forename: Yu Jia
authors.initials: YJ
authors.lastname: Tan
authors.forename: Jimei
authors.initials: J
authors.lastname: Ma
authors.forename: Min Li
authors.initials: ML
authors.lastname: Leow
authors.forename: Davin
authors.initials: D
authors.lastname: Tirtorahardjo
authors.forename: Xue-Wei
authors.initials: XW
authors.lastname: Liu
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D010165:Palladium; D011714:Pyrans / Q000138:chemical synthesis*
chemical_list: D000498:Allyl Compounds; D000900:Anti-Bacterial Agents; D011714:Pyrans; C432457:centrolobin; C000589853:decytospolide A; C000589854:decytospolide B; D010165:Palladium
keywords: centrolobine; decytospolides; stereoselectivity; tetrahydropyrans; total synthesis