Synfacts 2008(4): 0341-0341  
DOI: 10.1055/s-2008-1042880
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Spirofungin A

Contributor(s): Philip Kocienski
J. Marjanovic, S. A. Kozmin*
University of Chicago, USA
Further Information

Publication History

Publication Date:
19 March 2008 (online)


Spirofungin A is a metabolite of Streptomyces violaceuniger Tu 4113 that displays significant antiproliferative activity in a panel of cancer lines and it selectively inhibits isoleucyl-tRNA synthetase in mammalian cells. The synthesis depicted makes elegant use of ring-opening, ring-closing and cross metatheses mediated by Grubbs II catalyst to assemble key fragments. A further asset is the use of a temporary silylacetal tether to fix the stereochemistry of the spiroacetal at C15 in G.