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Synfacts 2007(2): 0122-0122  
DOI: 10.1055/s-2006-955761
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Acylfulvene and (-)-Irofulven

Contributor(s): Philip Kocienski, Fiona Black
M. Movassaghi*, G. Piizzi, D. S. Siegel, G. Piersanti
Massachusetts Institute of Technology, Cambridge, USA
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Publikationsverlauf

Publikationsdatum:
23. Januar 2007 (online)

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Significance

(-)-Irofulven is a semisynthetic derivative of the sesquiterpenes illudin M and illudin S and is in phase II clinical trials for the treatment of several types of cancer. The C2 stereocenter is installed using an Evans copper-catalyzed asymmetric aldol addition and the ring system is constructed via an enyne ring-closing metathesis.