Enantioselective syntheses of cryptocarya triacetate,cryptocaryolone, and cryptocaryolone diacetate |
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Authors: | Smith Catherine M O'Doherty George A |
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Affiliation: | Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA. |
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Abstract: | [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. |
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