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| - Synthesis of Tuckolide, a New Cholesterol Biosynthesis Inhibitor
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| - Tuckolide (decarestrictine D), a 10-membered lactone isolated fromP. corylophilum and polyporustuberaster fungi that potently inhibits cholesterol biosynthesis,was synthesized. The key stepsinclude a Sharpless catalytic asymmetric dihydroxylation reaction (AD)of the methoxymethyl(MOM) ether protected diene 2 and a direct Corey−Nicolaoulactonization reaction of seco-acid 1with added silver perchlorate. The selectivity of thedihydroxylation step was found to be highlydependent on the nature of the protecting group adjacent to the dienein 2. The selectivity of theasymmetric dihydroxylation reaction of 2 indicates that bothsteric and electronic effects can leadto significant amounts of the undesired isomers. This synthesisestablishes the absolute stereochemistry of tuckolide showing the C3 hydroxyl bearing carbon with anS-configuration comparablein an absolute sense to that in the lactone portion of the HMG-CoAreductase inhibitor compactin.
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