Download PDF
Synfacts 2008(9): 0903-0903  
DOI: 10.1055/s-2008-1077994
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Clausamines A-C

Contributor(s):Philip Kocienski, Indu Dager
T. P. Lebold, M. A. Kerr*
The University of Western Ontario, London, Canada
Total Synthesis of Clausamines A-C and Clausevatine D
Org. Lett.  2008,  10:  997-1000  
Crossref
Further Information

Publication History

Publication Date:
22 August 2008 (online)

 PDF Download Permissions and Reprints

Key words

clausamines A-C - clausevatines D-G - Diels-Alder reaction - Sharpless asymmetric dihydroxylation

Significance

Clausamines A-C are isolated from the Clausena anisata while clausevatines D-G and clausamines D-G were isolated from the root bark of Clausena excavata, which is used as a folk medicine for the treatment of snakebites, abdominal pain and as a detoxificant. The first total syntheses of clausamines A-C are reported here.

Comment

A Diels-Alder reaction between imine quinone A and cyclic diene B gave C in a highly regio­selective manner. In contrast to an optical rotation of zero reported for these natural products, the authors report a strong positive optical rotation for the R-enantiomer of these natural products.

   Permissions and Reprints