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Synfacts 2007(9): 0904-0904  
DOI: 10.1055/s-2007-968832
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of Platensimycin

Contributor(s): Philip Kocienski, Indu Dager
Y. Zou, C.-H. Chen, C. D. Taylor, B. M. Foxman, B. B. Snider*
Brandeis University, Waltham, USA
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

Antibiotic platensimycin is isolated from Streptomyces platensis and inhibits the FabF enzyme. A short synthesis of an advanced intermediate J in Nicolaou’s total synthesis of (±)-platensimycin is reported here (K. C. Nicolaou, A. Li, D. J. Edmonds Angew. Chem. Int. Ed. 2006, 45, 7086). The key step, an efficient radical cyclization by which enone D is converted into the tricyclic dione E, was also employed by Nicolaou and co-workers in their synthesis of (±)-platensimycin (Chem. Commun. 2007, 1922).