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Synfacts 2008(2): 0120-0120  
DOI: 10.1055/s-2007-992495
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Artochamins H, I, and J

Contributor(s): Philip Kocienski, Arndt W. Schmidt
K. C. Nicolaou*, T. Lister, R. M. Denton, C. F. Gelin
The Scripps Research Institute and University of California at San Diego, La Jolla, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Artochamins F, H, I and J were isolated from the roots of Artocarpus chama which is used in South-East Asian folk medicine. A cascade of [3,3]-sigmatropic rearrangements followed by an unusual thermally induced formal [2+2] cycloaddition (F→G) created the bicyclo[3.2.0]heptane framework. The artochamins H-J were synthesized in 9 to 10 steps via the common intermediate G.