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Synfacts 2006(4): 0310-0310  
DOI: 10.1055/s-2006-932035
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Rhazinilam

Contributor(s): Philip Kocienski
A. J. Bowie, C. C. Hughes, D. Trauner*
University of California at Berkeley, USA
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

The synthesis of Rhazinilam features a rare Heck-type cross-coupling between an unactivated pyrrole and an arylpalladium(II) intermediate to generate a strained nine-membered ring. A relatively high catalyst loading (10 mol%) and the use of Buchwald’s DavePhos ligand (E) were essential to succeed (S. L. Buchwald et al. J. Org. Chem. 1999, 64, 6019-6022). Similar conditions were recently applied to the difficult synthesis of the seven-membered ring in Allocolchicine (M. LeBlanc, K. Fagnou Org. Lett. 2005, 7, 2849-2852).