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Synfacts 2008(2): 0113-0113  
DOI: 10.1055/s-2007-992503
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Grandisine A

Contributor(s): Philip Kocienski
D. J. Maloney, S. J. Danishefsky*
Memorial Sloan-Kettering Cancer Center and Columbia University, New York, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Grandisine A is an indolizidine alkaloid isolated from Elaeocarpus grandis. It selectively (but weakly) binds to the δ-opioid receptor. The key step in the synthesis is a Lewis acid catalyzed Diels-Alder reaction that creates the stereogenic centers at C7 and C12 with the correct relative configuration.