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Synfacts 2007(12): 1231-1231  
DOI: 10.1055/s-2007-991306
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of (-)-Platensimycin

Contributor(s): Philip Kocienski, Zofia Komsta
P. Li, J. N. Payette, H. Yamamoto*
The University of Chicago, USA
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Publikationsdatum:
22. November 2007 (online)

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Significance

(-)-Platensimycin, isolated from a strain of Streptomyces platensis, is an antibiotic with a novel mechanism of action. The focal step of the synthesis is an enantio- and regioselective Diels-Alder reaction, promoted by a Brønsted acid assisted chiral Lewis acid (C + D). For asymmetric Diels-Alder reactions of substituted cyclopentadienes, see: J. N. Payette, H. Yamamoto J. Am. Chem. Soc. 2007, 129, 9536.