Stereoselective Synthesis of (S)- and (N)-Cyclopropyl-Fused Carbocyclic Nucleosides Using Stereoselective Cyclopropanation.

Young Eum Hyun, Hong-Rae Kim, Lak Shin Jeong

The Journal of organic chemistry 2021 Jul 16

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To determine which sugar conformation is favorable in binding to peroxisome proliferator-activated receptors, the conformationally locked south (S) and north (N) analogues were asymmetrically synthesized using a bicyclo[3.1.0]hexane template. The (S)-conformer was synthesized by employing "reagent-controlled" Charette asymmetric cyclopropanation in a 100% stereoselective manner, whereas the (N)-conformer was stereoselectively synthesized by using "substrate-controlled" hydroxyl-directed Simmons-Smith cyclopropanation as a key step.

Citation

Young Eum Hyun, Hong-Rae Kim, Lak Shin Jeong. Stereoselective Synthesis of (S)- and (N)-Cyclopropyl-Fused Carbocyclic Nucleosides Using Stereoselective Cyclopropanation. The Journal of organic chemistry. 2021 Jul 16;86(14):9828-9837