Synthesis of Tuckolide, a New Cholesterol Biosynthesis Inhibitor

機構典藏 > College of Sciences > Graduate Institute & Department of Chemistry > Journal Article > Item 987654321/25309

Please use this identifier to cite or link to this item: https://tkuir.lib.tku.edu.tw/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:	[Graduate Institute & Department of Chemistry] Journal Article

Files in This Item:

File	Description	Size	Format
		0Kb	Unknown	350	View/Open
Synthesis of Tuckolide, a New Cholesterol Biosynthesis Inhibitor.pdf		324Kb	Adobe PDF	1	View/Open