Enantioselective syntheses of cryptocarya triacetate, cryptocaryolone, and cryptocaryolone diacetate.
[reaction: see text] The enantioselective syntheses of three natural products from Cryptocarya latifolia have been achieved in 13-15 steps from ethyl sorbate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to establish the absolute stereochemistry. The route also relies upon a highly (E)-selective olefin cross-metathesis reaction to form trans-delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates were subsequently converted into cryptocarya triacetate, cryptocaryolone, and cryptocaryolone diacetate.
Smith
Catherine M
CM
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
O'Doherty
George A
GA
D000085:Acetates / Q000737:chemistry; D031369:Cryptocarya / Q000737:chemistry*; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis*; D007527:Isoenzymes / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D011451:Prostaglandin-Endoperoxide Synthases / Q000378:metabolism; D011753:Pyrones / Q000138:chemical synthesis* / Q000494:pharmacology; D013019:South Africa
D000085:Acetates; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D011753:Pyrones; C476917:cryptocarya triacetate; C476918:cryptocaryolone; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases