Design, Synthesis, and Resolution of Spirocyclic Bisoxindole-Based C2-Symmetric Diols
- 21 August 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (16), 10584-10592
- https://doi.org/10.1021/acs.joc.0c01155
Abstract
A new type of spirocyclic bisoxindole-based C-2-symmetric diols (SBIDOLs) was designed and synthesized. A series of racemic SBIDOL derivatives (6a-6g) were readily synthesized from commercially available 2-halo-S-methoxyanilines 1 (X = Cl or Br) through N-mono alkylation, acylation, oxidation, double intramolecular Friedel-Crafts reaction, and demethylation reactions. The optical resolution of racemic 6b was achieved via fractional crystallization of their bis-L-menthoxycarboxylates. Further modifications of SBIDOLs were investigated, leading to 5,5'-diaryl SBIDOL derivatives (11a and 11b) through Pd-catalyzed Suzuki coupling and DM-SBIDOL 12 by Pd/C-catalyzed hydrogenative dechlorination reactions.Funding Information
- Guangzhou Science and Technology Program key projects (201707020046)
- tate Key Laboratory of Anti-Infective Drug Development, Sunshine Lake Pharma Co. (2015DQ780357)
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