Organic Letters
Letter
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with TFA discovered earlier could now be used to our
advantage. Treatment of 17 with TFA gave the deiodinated and
Boc-deprotected intermediate, which was directly desilylated
using TBAF to provide breitfussin B, 2, in 67% yield over the
two steps and in a total yield of 4.3% from 3.
(9) LaPorte, M. G.; Jackson, R. W.; Draper, T. L.; Gaboury, J. A.;
Galie, K.; Herbertz, T.; Hussey, A. R.; Rippin, S. R.; Benetatos, C. A.;
Chunduru, S. K.; Christensen, J. S.; Coburn, G. A.; Rizzo, C. J.;
Rhodes, G.; O’Connell, J.; Howe, A. Y. M.; Mansour, T. S.; Collett, M.
S.; Pevear, D. C.; Young, D. C.; Gao, T.; Tyrrell, D. L. J.; Kneteman,
N. M.; Burns, C. J.; Condon, S. M. ChemMedChem 2008, 3, 1508.
(10) Fedouloff, M.; Hossner, F.; Voyle, M.; Ranson, J.; Powles, J.;
Riley, G.; Sanger, G. Bioorg. Med. Chem. 2001, 9, 2119.
(11) Vedejs, E.; Barda, D. A. Org. Lett. 2000, 2, 1033.
1
Finally, comparison of the 13C and H NMR spectra at 600
MHz of 1 and 2 in DMSO-(d6) proved to fully align with
previously reported spectral data1 (Supporting Information),
thus verifying the reported structure of the breitfussin
framework. In summary, we have prepared the natural products
breitfussin A and B in 7.2% and 4.3% overall yields, respectively
(from 3).
(12) Primas, N.; Bouillon, A.; Lancelot, J.-C.; Rault, S. Tetrahedron
2009, 65, 6348.
(13) Palmer, D. C.; Venkatraman, S. Synthesis and Reactions of
Oxazoles. In Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A;
John Wiley & Sons, Inc.: 2003; p 1.
ASSOCIATED CONTENT
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S
* Supporting Information
(14) (a) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011.
(b) Flegeau, E. F.; Popkin, M. E.; Greaney, M. F. J. Org. Chem. 2008,
73, 3303. (c) Li, B.; Buzon, R. A.; Zhang, Z.; Koshiba, T.; Fukuyama,
T. Org. Synth. 2010, 87, 16. (d) Williams, D. R.; Fu, L. Org. Lett. 2010,
12, 808.
Experimental procedures, spectroscopic details, and a compar-
1
ison of the H and 13C NMR data of natural and synthetic 1
and 2. This material is available free of charge via the Internet at
AUTHOR INFORMATION
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Corresponding Authors
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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The Research Council of Norway has supported this work by a
grant to S.K.P. (224790/O30) and a travel grant to Y.G.
(MabCent, 174885). Y.G. and A.B. wish to thank Prof. Trond
Ø. Jørgensen (UiT The Arctic University of Norway) for his
generous support.
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