Organic Letters
Letter
(16) Devi, A. R.; Rajaram, S. Indian J. Chem., Sect. B 2000, 39B, 294.
(17) Podlech, J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1995, 34,
471.
and a final anhydrous acid promoted hemiacetal formation
concluded the synthesis.
(18) Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761.
(19) Node, M.; Nishide, K.; Fuji, K.; Fujita, E. J. Org. Chem. 1980, 45,
4275.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
(20) McOmie, J. F. W.; West, D. E. Org. Synth. 1969, 49, 50.
1
(21) Determined by H NMR.
(22) Beugelmans, R.; Bourdet, S.; Bigot, A.; Zhu, J. Tetrahedron Lett.
1994, 35, 4349.
(23) We cannot rule out silyl migration to an aliphatic alcohol under
Experimental procedures, characterization of products,
crystallographic information for compound 18 and 21,
these reactions.
1
and H and 13C NMR spectra (PDF)
(24) Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey,
D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6436.
Crystallographic data for 18 (CIF)
Crystallographic data for 21 (CIF)
AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are grateful to the NIH for generous support of this work
(R01GM117570) and to NC State University for support of
our program. Mass spectrometry data were obtained at the NC
State Mass Spectroscopy Facility. We thank Dr. Roger Sommer
(NC State) for X-ray crystallographic analysis of 18 and 21.
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Org. Lett. XXXX, XXX, XXX−XXX