Synthesis of cyclitols via cyclopropanation/palladium-catalyzed ring opening.

[摘要]：The stereoselective syntheses of three cyclitols, 5a-carba-a-D-rhamnopyranose, 5a-carba-b-D-digitoxopyranose, and 5a-carba-a-L-rhamnopyranose, have been achieved. The routes rely upon a Simmons-Smith cyclopropanation and diastereospecific ring opening of cyclopropanol under Pd/C hydrogenation conditions to prep. 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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