Stereoselective construction of the tricyclic core of neoliacinic acid.
The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.
Clark
J Stephen
JS
WestCHEM, Department of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow, G12 8QQ, United Kingdom. stephenc@chem.gla.ac.uk
Baxter
Carl A
CA
Dossetter
Alexander G
AG
Poigny
Stéphane
S
Castro
José L
JL
Whittingham
William G
WG
D001391:Azo Compounds / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004951:Esterification; D004986:Ether / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
D001391:Azo Compounds; D001688:Biological Products; D001965:Bromides; D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; D007783:Lactones; D020005:Propanols; C527591:neoliacinic acid; D004986:Ether; C006463:allyl alcohol