Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (gamma)- and pyranyl (delta)-lactols.

Journal article

Tetrahydropyran and tetrahydrofuran containing natural products, drugs and agrochemicals often possess carbon-carbon bonds adjacent to the heteroatom. Consequently, new methods for the construction of anomeric carbon-carbon bonds are of considerable importance. We have devised a new strategy to access these systems that requires the treatment of O-glycoside alkynyl tributylstannane derivatives of furanyl and pyranyl lactols with Lewis acid to effect oxygen to carbon rearrangements. This leads...

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Authors: Buffet, M; Dixon, D; Ley, S; Reynolds, D; Storer, R

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 2
• Issue: 8
• Pages: 1145-1154
• Publication date: 2004-04-01
• DOI: 10.1039/b316858a
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English
• Keywords: Pyrans; Lipoxygenase Inhibitors; Furans; Carbon; Lactones; Trialkyltin Compounds; Enzyme Inhibitors; Alkynes; Animals; Oxygen; Crystallography, X-Ray