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Totally Synthetic by Paul H. Docherty, 31 May 2006

Total Synthesis of Yatakemycin


K. Okano, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2006, 128, 7136-7137.

DOI: 10.1021/ja0619455

Continuing with a heterocyclic theme, Fukuyama has published a short (20 steps), flexible and rather sweet (13% yield) total synthesis of yakatemycin. Especially interesting is his use of a ring contraction to install the cyclopropane:

Completed as the final step in the synthesis, one can imagine several fingers were crossed during the reaction! This paper also includes the use of an azide displacement / Staudinger reaction to create a β-hydroxy amine from a chlorohydrin. Monoprotection of the amine with a nosyl group then allowed them to complete a ring-closing amination.

Although the nosyl group is fairly well known, I thought I'd show it in full: