Organic Letters
Letter
(14) Isolation: Schmitz, F. J.; Hollenbrek, K. H.; Vanderah, D. J.
Tetrahedron 1978, 34, 2719−2722. Selected syntheses: Gadwood, R.
C.; Lett, R. M.; Wissinger, J. E. J. Am. Chem. Soc. 1986, 108, 6343−
6350. Feldman, K. S.; Wu, M. -; Rotella, D. P. J. Am. Chem. Soc. 1990,
112, 8490−8496. Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1995,
60, 4559−4565. Harmata, M.; Rashatasakhon, P. Org. Lett. 2000, 2,
2913−2915. Yun, S.; Hansen, E.; Volchkov, I.; Cho, E.; Lo, W.; Lee, D.
Angew. Chem., Int. Ed. 2010, 49, 4261−4263. Dowling, M. S.;
Vanderwal, C. D. J. Org. Chem. 2010, 75, 6908−6922.
here and the application of these chemistries to the synthesis of
dactylol are currently under study.
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
(15) Effenberger, F.; Ziegler, T.; Schonwalder, K.; Kesmarszky, T.;
̈
̈
Crystallographic data for 23 (CIF)
Crystallographic data for 24 (CIF)
Experimental details, spectra for new compounds, and
computational details (PDF)
Bauer, B. Chem. Ber. 1986, 119, 3394−3404.
(16) Oikawa, H.; Kobayashi, T.; Katayama, K.; Suzuki, Y.; Ichihara, A.
J. Org. Chem. 1998, 63, 8748−8756.
(17) Bansal, V.; Kanodia, S.; Thapliyal, P. C.; Khanna, R. N. Synth.
Commun. 1996, 26, 887−892.
(18) Sieburth, S. McN.; Lin, C.-H. J. Org. Chem. 1994, 59, 3597−
3599.
AUTHOR INFORMATION
Corresponding Author
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(19) Yoo, H. Y.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 2877−
2884.
(20) Aviyente, V.; Houk, K. N. J. Phys. Chem. A 2001, 105, 383−391.
(21) Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187−
10198.
Notes
The authors declare no competing financial interest.
(22) Levy, H.; Cope, A. C. J. Am. Chem. Soc. 1944, 66, 1684−1688.
von E. Doering, W.; Roth, W. R. Tetrahedron 1963, 19, 715−737.
(23) Vogel, E.; Ott, K.-H.; Gajek, K. Eur. J. Org. Chem. 1961, 644,
172−188.
ACKNOWLEDGMENTS
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We gratefully acknowledge support from the National Science
Foundation (1152159) and Professor Steven A. Fleming
(Temple Univ.) for helpful discussions. We also thank
Professor Michael J. Zdilla (Temple Univ.), Dr. Shivaiah
Vaddypally (Temple Univ.), and Charles M. Stockdale
(Temple Univ.) for the crystal structures.
(24) Schroder, G. Angew. Chem., Int. Ed. Engl. 1963, 2, 481−482.
̈
Hudlicky, T.; Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org. React.
1992, 41, 1−133. Williams, R. V. Eur. J. Org. Chem. 2001, 2001, 227−
235.
(25) Vogel, E. Liebigs. Ann. Chem. 1958, 615, 1−14.
(26) Huntsman, W. D.; De Boer, J. A.; Woosley, M. H. J. Am. Chem.
Soc. 1966, 88, 5846−5850.
REFERENCES
■
(27) Navarro-Vaz
6, 2981−2984.
́
quez, A.; Prall, M.; Schreiner, P. R. Org. Lett. 2004,
(1) Sieburth, S. McN. Photochemical reactivity of pyridones. In CRC
Handbook of Organic Photochemistry and Photobiology; Horspool, W.,
Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; Chapter 103, pp 1−
18.
(28) Graulich, N. Wiley. Interdiscip. Rev. Comput. Mol. Sci. 2011, 1,
172−190.
(29) The relative energies calculated for 24 and 27 varied
significantly depending on the method used.
(2) Shimo, T.; Somekawa, K. Photocycloaddition Reactions of 2-
Pyrones. In CRC Handbook of Organic Photochemistry and Photo-
biology; Horspool, W., Lenci, F., Eds.; CRC Press: Boca Raton, FL,
2004; Chapter 82, pp 1−19.
(3) West, F. G. Photocyclization and Photocycloaddition Reactions
of 4- and 2-Pyrones. In Advances in Cycloaddition; Lautens, M., Ed.; JAI
Press: Greenwich, CT, 1997; 1−40. Song, D.; McDonald, R.; West, F.
G. Org. Lett. 2006, 8, 4075−4078. Li, L.; McDonald, R.; West, F. G.
Org. Lett. 2008, 10, 3733−3736. Li, L.; Bender, J. A.; West, F. G.
Tetrahedron Lett. 2009, 50, 1188−1192.
(30) Price, J. D.; Johnson, R. P. Tetrahedron Lett. 1986, 27, 4679−
4682. see also: Angus, R. O.; Schmidt, M. W.; Johnson, R. P. J. Am.
Chem. Soc. 1985, 107, 532−537. Price, J. D.; Johnson, R. P. J. Org.
Chem. 1991, 56, 6372−6376. Daoust, K. J.; Hernandez, S. M.; Konrad,
K. M.; Mackie, I. D.; Winstanley, J.; Johnson, R. P. J. Org. Chem. 2006,
71, 5708−5714.
(4) Taylor, E. C.; Paudler, W. W. Tetrahedron Lett. 1960, 1, 1−3.
(5) de Mayo, P.; Yip, R. W. Proc. Chem. Soc. 1964, 84.
(6) Sieburth, S. McN.; Chen, J. L. J. Am. Chem. Soc. 1991, 113,
8163−8164. Sieburth, S. McN.; Lin, C.-H. J. Org. Chem. 1994, 59,
3597−3599. Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J.-L. J.
Am. Chem. Soc. 1996, 118, 10803−10810. Sieburth, S. McN.; McGee,
K. F. Org. Lett. 1999, 1, 1775−1777. Lee, Y.-G.; McGee, K. F.; Chen,
J.; Rucando, D.; Sieburth, S. McN. J. Org. Chem. 2000, 65, 6676−6681.
(7) Sieburth, S. McN.; McGee, K. F.; Zhang, F.; Chen, Y. J. Org.
Chem. 2000, 65, 1972−1977.
(8) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58,
3794−3795.
(9) Khatri, B. B.; Vrubliauskas, D.; Sieburth, S. McN. Tetrahedron
Lett. 2015, 56, 4520−4522.
(10) Nakamura, Y.; Kato, T.; Morita, Y. J. Chem. Soc., Chem.
Commun. 1978, 620−621.
(11) Kulyk, S.; Dougherty, W. G., Jr.; Kassel, W. S.; Fleming, S. A.;
Sieburth, S. McN. Org. Lett. 2010, 12, 3296−3299.
(12) Kulyk, S.; Khatri, B. B.; Sieburth, S. McN. Org. Lett. 2014, 16,
4138−4141.
(13) Khatri, B. B.; Kulyk, S.; Sieburth, S. McN. Org. Chem. Front.
2014, 1, 961−964.
D
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