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Synfacts 2007(6): 0573-0573  
DOI: 10.1055/s-2007-968512
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of (+)-Galbulimima Alkaloid 13 and (+)-Himgaline

Contributor(s): Philip Kocienski, Thomas Snaddon
D. A. Evans, D. J. Adams*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

The Galbulimima alkaloids are isolated from Galbulimima belgraveana, a tree with a long history in tribal medicine. Key to this synthesis is (1) a diastereoselective intramolecular Diels-Alder reaction to prepare the trans-decalin core, and (2) a Roskamp-Michael addition sequence to install the cis-fused 5,6-ring junction. For a recent asymmetric synthesis of (+)- and (-)-galbulimima alkaloid 13, see: M. Movassaghi, D. K. Hunt, M. Tjandra J. Am. Chem. Soc. 2006, 128, 8126-8127.