Glutarimide Antibiotics. IV. The Total Synthesis of <i>dl-</i> and <i>l-</i>Cycloheximide

Johnson, Francis; Starkovsky, Nicolas A.; Paton, A. C.; Carlson, Alena

doi:10.1021/ja01055a030

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2014

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Cited by 28 publications

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“…Using a milder base could largely avoid the racemization problem. Treating 6b (er of 87:13) in methanol/water (4/1) mixture solvent containing 1.1 equiv of collidine at room temperature for 1.5 h gave (1 S ,2 R )-diol monoisobutyrate 6c (er of 86:14) in 93% isolated yield . The enantiomerically enriched 6c is stable in aprotic solvents such as CH 2 Cl 2 solution for at least 3 days at room temperature and this period is long enough for carrying further organic transformations.…”

Section: Resultsmentioning

confidence: 99%

Desymmetrization of meso-1,2-Diols via the Dynamic Kinetic Resolution of Its Monodichloroacetates

Cao

2010

J. Org. Chem.

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Enantioselective acylation catalyzed by the thioamide modified 1-methylhistidine methyl ester 1 in combination with DABCO-mediated racemization of the substrate led to the efficient dynamic kinetic resolution of meso-1,2-diol monodichloroacetates. In this way, cyclic and acyclic meso-1,2-diol monodichloroacetates can be transformed to the enantiomerically enriched (1S,2R)-heterosubstituted diol diesters which are stable in enantiomerically pure form and can be readily used for further organic transformations.

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Section: Resultsmentioning

confidence: 99%