Facile Construction of the Colchicine Skeleton By a Rhodium-Catalyzed Cyclization/Cycloaddition Cascade

Abstract

The major alkaloid of the meadow saffron is colchicine, which displays remarkable antimitotic activity and has long been used in the treatment of acute gout and is currently being tested against a broad variety of other diseases. In a remarkable Rh-catalyzed domino transformation, the complete carbon skeleton of this important alkaloid is assembled with high efficiency (see scheme). TBS=tert-butyldimethylsilyl, TMS=trimethylsilyl. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z18522_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.