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Synfacts 2008(9): 0897-0897  
DOI: 10.1055/s-2008-1077984
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Rhazinicine

Contributor(s): Philip Kocienski, Stewart Eccles
E. M. Beck, R. Hatley, M. J. Gaunt*
University of Cambridge and GlaxoSmithKline, Stevenage, UK
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

Rhazinacine is a member of the rhazinilam family of natural products that mimic the cellular effects of paclitaxel. The synthesis of rhazinicine has two noteworthy steps: (1) the C-H functionalization of an N-protected pyrrole (A → C); (2) a palladium(II)-catalyzed intramolecular alkenylation to set up the tetrahydro­indolizine ring system (E → F).