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Issue 22, 2012
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Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction

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Abstract

Optically active ent-calystegine B4 was prepared in 13 steps from commercially available chiral L-dimethyl tartrate. The synthesis was achieved by the Michael addition and the aldol reaction of nitromethane to form cycloheptanone in a stereoselective manner. Reduction of the nitro group in the presence of Boc2O accomplished an efficient conversion to amino cycloheptanone, which readily afforded the desired ent-calystegine B4.

Graphical abstract: Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction

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Publication details

The article was received on 22 Feb 2012, accepted on 10 Apr 2012 and first published on 13 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB25386K
Citation: Org. Biomol. Chem., 2012,10, 4362-4366
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    Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction

    A. Kamimura, K. Miyazaki, S. Suzuki, S. Ishikawa and H. Uno, Org. Biomol. Chem., 2012, 10, 4362
    DOI: 10.1039/C2OB25386K

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