Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 22, 2012
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

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
  •   Request permissions

    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

Search articles by author