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Synfacts 2006(2): 0107-0107
DOI: 10.1055/s-2005-924813
DOI: 10.1055/s-2005-924813
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Anisomycin
S. Kaden, M. Brockmann, H.-U. Reissig*
Freie Universität Berlin, Germany
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2006 (online)


Significance
(-)-Anisomycin is a metabolite of Streptomyces grisoleaus and S. roseochromogenes with fungicidal and in vitro antitumor activity. Synthetic routes to the 3-alkoxy (or hydroxy) pyrrolidine core are of interest as this moiety is found in a number of biologically active natural products. The synthesis of both enantiomers of anisomycin is reported. The most interesting step in this synthesis, the cyclization of the alkoxyallene C to the dihydropyrrole D, is compromised somewhat by the use of a 12-carbon chiral auxiliary to deliver a 3-carbon allene unit with only modest stereoselectivity.