Synthesis of Carba-Sugar C-1 Phosphates via Pd-Catalyzed Cyclopropanol Ring Opening.

[摘要]：The stereoselective syntheses of 2,3-dideoxy-4-oxo-5a-carba-a-D-rhamnopyanose 1-phosphate, 2,3-dideoxy-5a-carba-a-D-rhamnopyranose 1-phosphate, 5a-carba-a-D-rhamnopyranose 1-phosphate, 5a-carba-b-D-digitoxopyranose 1-phosphate, and 5a-carba-a-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 a-Me ketone. A sequence of diastereoselective redn., dihydroxylation, and/or Myers' reductive 1,3-rearrangement were used to install the desired stereochem.

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