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Updated: Jul 3, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Synthesis of carbasugar C-1 phosphates via Pd-catalyzed cyclopropanol ring opening
Mingde Shan1, George A O'Doherty
1Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Abstract:
The stereoselective syntheses of 2,3-dideoxy-4-oxo-5a-carba-alpha- d-rhamnopyanose 1-phosphate, 2,3-dideoxy-5a-carba-alpha- d-rhamnopyranose 1-phosphate, 5a-carba-alpha- d-rhamnopyranose 1-phosphate, 5a-carba-beta- d-digitoxopyranose 1-phosphate, and 5a-carba-alpha- l-rhamnopyranose 1-phosphate have been achieved from d-quinic acid. The routes rely upon a Simmons-Smith cyclopropanation and diastereospecific ring opening of cyclopropanol under Pd/C hydrogenation condition to set up the alpha-methyl ketone. A sequence of diastereoselective reduction, dihydroxylation, and/or Myers' reductive 1,3-rearrangement were used to install the desired stereochemistry.
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