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    Please use this identifier to cite or link to this item: http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/25309


    Title: Synthesis of Tuckolide, a New Cholesterol Biosynthesis Inhibitor
    Authors: Andrus, M. B.;Shih, Tzenge-Lie;施增廉
    Contributors: 淡江大學化學學系
    Date: 1996-12-13
    Issue Date: 2009-12-01
    Publisher: American Chemical Society (ACS)
    Abstract: Tuckolide (decarestrictine D), a 10-membered lactone isolated from P. corylophilum and polyporus tuberaster fungi that potently inhibits cholesterol biosynthesis, was synthesized. The key steps include a Sharpless catalytic asymmetric dihydroxylation reaction (AD) of the methoxymethyl (MOM) ether protected diene 2 and a direct Corey−Nicolaou lactonization reaction of seco-acid 1 with added silver perchlorate. The selectivity of the dihydroxylation step was found to be highly dependent on the nature of the protecting group adjacent to the diene in 2. The selectivity of the asymmetric dihydroxylation reaction of 2 indicates that both steric and electronic effects can lead to significant amounts of the undesired isomers. This synthesis establishes the absolute stereochemistry of tuckolide showing the C3 hydroxyl bearing carbon with an S-configuration comparable in an absolute sense to that in the lactone portion of the HMG-CoA reductase inhibitor compactin.
    Relation: Journal of Organic Chemistry 61(25), pp.8780-8785
    DOI: 10.1021/jo961686+
    Appears in Collections:[化學學系暨研究所] 期刊論文

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