D-Ribofuranose and D-arabinofuranose derivatives were converted in a few steps into their 1,4-diketone derivatives, which were pinacol cyclised under the action of SmI2 to form the corresponding chiral cyclobutanediol products. These products can potentially be applied to the synthesis of anti-viral agents, some of whose structures incorporate chiral cyclobutanediol moieties.
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http://dx.doi.org/10.1016/j.carres.2005.02.006 | DOI Listing |
ACS Omega
April 2024
Sanken, Osaka University, 8-1 Mihogaoka, Ibaraki 567-0047, Osaka, Japan.
A practical synthesis of -1,4-dialdehydes based on the oxidative cleavage of cyclobutanediol derivatives using polymer-supported periodate was developed. The -1,4-dialdehydes were obtained in up to >99% yield and subsequently employed in Ir-catalyzed asymmetric Tishchenko reactions to give the corresponding chiral lactones, which are versatile synthetic intermediates, in good yield with moderate enantiomeric excess. The catalytically active species was identified by means of cold-spray ionization mass spectrometry and H NMR spectroscopy.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2017
Department of Chemistry, Department of Phamacology, Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Rd, Evanston, IL, 60208, USA.
The Armillaria and Lactarius genera of fungi produce the antimicrobial and cytotoxic mellolide, protoilludane, and marasmane sesquiterpenoids. We report a unified synthetic strategy to access the protoilludane, mellolide, and marasmane families of natural products. The key features of these syntheses are 1) the organocatalytic, enantioselective construction of key chiral intermediates from a simple achiral precursor, 2) the utility of a key 1,2-cyclobutanediol intermediate to serve as a precursor to each natural product class, and 3) a direct chemical conversion of a protoilludane to a marasmane through serendipitous ring contraction, which provides experimental support for their proposed biosynthetic relationships.
View Article and Find Full Text PDFCarbohydr Res
May 2005
Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, 2006, South Africa.
D-Ribofuranose and D-arabinofuranose derivatives were converted in a few steps into their 1,4-diketone derivatives, which were pinacol cyclised under the action of SmI2 to form the corresponding chiral cyclobutanediol products. These products can potentially be applied to the synthesis of anti-viral agents, some of whose structures incorporate chiral cyclobutanediol moieties.
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