Pure and Applied Chemistry

Pure Appl. Chem., 2013, Vol. 85, No. 10, pp. 1949-1957

http://dx.doi.org/10.1351/PAC-CON-12-11-22

Published online 2013-07-10

Inherent dynamical preferences in carbocation rearrangements leading to terpene natural products

References

• 1a. D. R. Glowacki, S. P. Marsden, M. J. Pilling. J. Am. Chem. Soc. 131, 13896 (2009). (http://dx.doi.org/10.1021/ja9043054)
• 1b. Z. Wang, J. S. Hirschi, D. A. Singleton. Angew. Chem., Int. Ed. 48, 9156 (2009). (http://dx.doi.org/10.1002/anie.200903293)
• 2. Y. Oyola, D. A. Singleton. J. Am. Chem. Soc. 131, 3130 (2009). (http://dx.doi.org/10.1021/ja807666d)
• 3. K. Black, P. Liu, L. Xu, C. Doubleday, K. N. Houk. Proc. Natl. Acad. Sci. USA 109, 12860 (2012). (http://dx.doi.org/10.1073/pnas.1209316109)
• 4. C. Doubleday, K. Bolton, W. L. Hase. J. Am. Chem. Soc. 119, 5251 (1997). (http://dx.doi.org/10.1021/ja964250k)
• 5a. L. M. Goldman, D. R. Glowacki, B. K. Carpenter. J. Am. Chem. Soc. 133, 5312 (2011). (http://dx.doi.org/10.1021/ja1095717)
• 5b. B. K. Carpenter. Ann. Rev. Phys. Chem. 56, 57 (2005). (http://dx.doi.org/10.1146/annurev.physchem.56.092503.141240)
• 5c. B. K. Carpenter. Acc. Chem. Res. 25, 520 (1992). (http://dx.doi.org/10.1021/ar00023a006)
• 5d. B. K. Carpenter. J. Phys. Org. Chem. 16, 858 (2003). (http://dx.doi.org/10.1002/poc.672)
• 6a. D. A. Singleton, C. Hang, M. J. Szymanski, E. E. Greenwald. J. Am. Chem. Soc. 125, 1176 (2003). (http://dx.doi.org/10.1021/ja027221k)
• 6b. D. A. Singleton, C. Hang, M. J. Szymanski, M. P. Meyer, A. G. Leach, K. T. Kuwata, J. S. Chen, A. Greer, C. S. Foote, K. N. Houk. J. Am. Chem. Soc. 125, 1319 (2003). (http://dx.doi.org/10.1021/ja027225p)
• 7. J. B. Thomas, J. R. Waas, M. Harmata, D. A. Singleton. J. Am. Chem. Soc. 130, 14544 (2008). (http://dx.doi.org/10.1021/ja802577v)
• 8. B. R. Ussing, C. Hang, D. A. Singleton. J. Am. Chem. Soc. 128, 7594 (2006). (http://dx.doi.org/10.1021/ja0606024)
• 9. L. Xu, C. E. Doubleday, K. N. Houk. J. Am. Chem. Soc. 132, 3029 (2010). (http://dx.doi.org/10.1021/ja909372f)
• 10. L. Xu, C. E. Doubleday, K. N. Houk. J. Am. Chem. Soc. 133, 17848 (2011). (http://dx.doi.org/10.1021/ja207051b)
• 11a. M. R. Siebert, J. Zhang, S. V. Addepalli, D. J. Tantillo, W. L. Hase. J. Am. Chem. Soc. 133, 8335 (2011). (http://dx.doi.org/10.1021/ja201730y)
• 11b. M. R. Siebert, R. Manikandan, D. J. Tantillo, W. L. Hase. J. Chem. Theory Comput. 8, 1212 (2012). (http://dx.doi.org/10.1021/ct300037p)
• 12. C. Gonzalez, H. B. Schlegel. J. Phys. Chem. 94, 5523 (1990). (http://dx.doi.org/10.1021/j100377a021)
• 13. K. Fukui. Acc. Chem. Res. 14, 363 (1981). (http://dx.doi.org/10.1021/ar00072a001)
• 14. Y. J. Hong, D. J. Tantillo. Nat. Chem. 1, 384 (2009). (http://dx.doi.org/10.1038/nchem.287)
• 15a. D. J. Tantillo. J. Phys. Org. Chem. 21, 561 (2008). (http://dx.doi.org/10.1002/poc.1320)
• 15b. A. Williams. Concerted Organic and Bio-Organic Mechanisms, CRC Press (2000); for a concerted triple shift rearrangement of a biologically relevant carbocation, see.
• 15c. Y. J. Hong, D. J. Tantillo. J. Am. Chem. Soc. 132, 5375 (2010). (http://dx.doi.org/10.1021/ja9084786)
• 15d. Y. J. Hong, R. Ponec, D. J. Tantillo. J. Phys. Chem. A 116, 8902 (2012). (http://dx.doi.org/10.1021/jp3047328)
• 16. D. J. Tantillo. Nat. Prod. Rep. 28, 1035 (2011). (http://dx.doi.org/10.1039/c1np00006c)
• 17. O. M. Gonzalez-James, E. E. Kwan, D. A. Singleton. J. Am. Chem. Soc. 134, 1914 (2012). (http://dx.doi.org/10.1021/ja208779k)
• 18a. Y. J. Hong, D. J. Tantillo. J. Am. Chem. Soc. 133, 18249 (2012). (http://dx.doi.org/10.1021/ja2055929)
• 18b. M. W. Lodewyk, P. Gutta, D. J. Tantillo. J. Org. Chem. 73, 6570 (2008). (http://dx.doi.org/10.1021/jo800868r)
• 18c. Y. J. Hong, D. J. Tantillo. J. Am. Chem. Soc. 131, 7999 (2009). (http://dx.doi.org/10.1021/ja9005332)
• 18d. Y. J. Hong, D. J. Tantillo. Chem. Sci. 1, 609 (2010). (http://dx.doi.org/10.1039/c0sc00333f)
• 18e. Y. J. Hong, D. J. Tantillo. Org. Lett. 13, 1294 (2011). (http://dx.doi.org/10.1021/ol103079v)
• 19a. M. Weitman, D. T. Major. J. Am. Chem. Soc. 132, 6349 (2010). (http://dx.doi.org/10.1021/ja910134x)
• 19b. M. Weitman, D. T. Major. J. Am. Chem. Soc. 134, 19454 (2012).
• 20. Reviews and leading references.
• 20a. J. B. Thomas, J. R. Waas, M. Harmata, D. A. Singleton. J. Am. Chem. Soc. 130, 14544 (2008). (http://dx.doi.org/10.1021/ja802577v)
• 20b. D. H. Ess, S. E. Wheeler, R. G. Iafe, L. Xu, N. Çelebi‑Ölçüm, K. N. Houk. Angew. Chem., Int. Ed. 47, 7592 (2008). (http://dx.doi.org/10.1002/anie.200800918)
• 20c. Y. J. Hong, D. J. Tantillo. Org. Biomol. Chem. 8, 4589 (2010). (http://dx.doi.org/10.1039/c0ob00167h)
• 21a. Y. J. Hong, D. J. Tantillo. Unpublished results.
• 21b. This material was first presented in a lecture by D. J. Tantillo at the 34^th Annual Reaction Mechanisms Conference, University of Missouri, Columbia, MO, June 19–22 (2012).
• 22. Leading references.
• 22a. D. J. Tantillo, J. Chen, K. N. Houk. Curr. Opin. Chem. Biol. 2, 743 (1998). (http://dx.doi.org/10.1016/S1367-5931(98)80112-9)
• 22b. D. J. Tantillo, K. N. Houk. “Theozymes and catalyst design” in Stimulating Concepts in Chemistry, pp. 79–88, Wiley-VCH, Weinheim (2000).
• 22c. J. DeChancie, F. R. Clemente, A. J. T. Smith, H. Gunaydin, Y.-L. Zhao, X. Zhang, K. N. Houk. Protein Sci. 16, 18516 (2007). (http://dx.doi.org/10.1110/ps.072963707)
• 23. Y. J. Hong, D. J. Tantillo. Org. Biomol. Chem. 8, 4589 (2010) and refs. therein. (http://dx.doi.org/10.1039/c0ob00167h)
• 24. For C–H···lone pair interactions, see.
• 24a. O. Takahashi, Y. Kohno, M. Nishio. Chem. Rev. 110, 6049 (2010). (http://dx.doi.org/10.1021/cr100072x)
• 24b. C. L. Perrin, J. B. Nielson. Ann. Rev. Phys. Chem. 48, 511 (1997). (http://dx.doi.org/10.1146/annurev.physchem.48.1.511)
• 24c. J. C. Ma, D. A. Dougherty. Chem. Rev. 97, 1303 (1997); for selected examples of C–H···π interactions involving carbocations, see.
• 24d. C. W. Jenson, L. Jorgensen. J. Am. Chem. Soc. 119, 10846 (1997). (http://dx.doi.org/10.1021/ja9714245)
• 24e. P. C. Miklis, R. Ditchfield, T. A. Spencer. J. Am. Chem. Soc. 120, 10482 (1998). (http://dx.doi.org/10.1021/ja980505d)
• 24f. H. Dietmar. Angew. Chem., Int. Ed. 41, 3208 (2002).
• 24g. F. Antonello, R. Graziella, R. Gabriele, G. Felice, S. Maurizio. Chem.—Eur. J. 9, 2072 (2003).
• 24h. Y. J. Hong, D. J. Tantillo. J. Org. Chem. 72, 8877 (2007). (http://dx.doi.org/10.1021/jo701526x)
• 24i. D. A. Dougherty. Science 271, 163 (1996). (http://dx.doi.org/10.1126/science.271.5246.163)
• 24j. D. Farcasiu, D. Hâncu. J. Phys. Chem. A 101, 8695 (1997). (http://dx.doi.org/10.1021/jp9714680)
• 24k. J. A. Faraldos, A. K. Antonczak, V. Gonzalez, R. Fullerton, E. M. Tippmann, R. K. Allemann. J. Am. Chem. Soc. 133, 13906 (2011). (http://dx.doi.org/10.1021/ja205927u)
• 24l. S. Kolboe. J. Phys. Chem. A 115, 3106 (2011). (http://dx.doi.org/10.1021/jp110283t)
• 24m. S. Kolboe. J. Phys. Chem. A 116, 3710 (2012). (http://dx.doi.org/10.1021/jp211731j)
• 24n. Y. J. Hong, D. J. Tantillo. Chem. Sci. 4, 2512 (2013). (http://dx.doi.org/10.1039/c3sc50571e)
• 25. D. J. Tantillo. Chem. Soc. Rev. 39, 2847 (2010). (http://dx.doi.org/10.1039/b917107j)
• 26a. D. W. Christianson. Chem. Rev. 106, 3412 (2006). (http://dx.doi.org/10.1021/cr050286w)
• 26b. D. A. Whittington, M. L. Wise, M. Urbansky, R. M. Coates, R. B. Croteau, D. W. Christianson. Proc. Natl. Acad. Sci. USA 99, 15375 (2002). (http://dx.doi.org/10.1073/pnas.232591099)
• 26c. W. Schwab, D. C. Williams, E. M. Davis, R. Croteau. Arch. Biochem. Biophys. 392, 123 (2001). (http://dx.doi.org/10.1006/abbi.2001.2442)
• 26d. M. L. Wise, T. J. Savage, E. Katahira, R. Croteau. J. Biol. Chem. 273, 14891 (1998). (http://dx.doi.org/10.1074/jbc.273.24.14891)
• 27a. C. A. Grob. Acc. Chem. Res. 16, 426 (1983). (http://dx.doi.org/10.1021/ar00096a001)
• 27b. H. C. Brown. Acc. Chem. Res. 16, 432 (1983). (http://dx.doi.org/10.1021/ar00096a002)
• 27c. G. A. Olah, G. K. S. Prakash, M. Saunders. Acc. Chem. Res. 16, 440 (1983). (http://dx.doi.org/10.1021/ar00096a003)
• 27d. C. Walling. Acc. Chem. Res. 16, 448 (1983). (http://dx.doi.org/10.1021/ar00096a004)
• 27e. H. C. Brown, with comments by P. v. R. Schleyer. The Nonclassical Ion Problem, Plenum, New York (1977).
• 27f. P. R. Schreiner, D. L. Severance, W. L. Jorgensen, P. v. R. Schleyer, H. F. Schaefer. J. Am. Chem. Soc. 117, 2663 (1995). (http://dx.doi.org/10.1021/ja00114a037)
• 27g. P. R. Schreiner, P. v. R. Schleyer, H. F. Schaefer. J. Org. Chem. 62, 4216 (1997). (http://dx.doi.org/10.1021/jo9613388)
• 27h. P. v. R. Schleyer, S. Sieber. Angew. Chem., Int. Ed. Engl. 32, 1606 (1993). (http://dx.doi.org/10.1002/anie.199316061)
• 28. S. P. T. Matsuda, W. K. Wilson, Q. Xiong. Org. Biomol. Chem. 4, 530 (2006). (http://dx.doi.org/10.1039/b513599k)
• 29. E. Y. Shishova, L. DiCostanzo, D. E. Cane, D. W. Christianson. Biochemistry 46, 1941 (2007). (http://dx.doi.org/10.1021/bi0622524)
• 30. For leading references on trichodiene biosynthesis, see.
• 30a. L. S. Vedula, Y. Zhao, R. M. Coates, T. Koyama, D. E. Cane, D. W. Christianson. Arch. Biochem. Biophys. 466, 260 (2007). (http://dx.doi.org/10.1016/j.abb.2007.06.016)
• 30b. L. S. Vedula, D. E. Cane, D. W. Christianson. Biochemistry 44, 12719 (2005). (http://dx.doi.org/10.1021/bi0510476)
• 30c. M. J. Rynkiewicz, D. E. Cane, D. W. Christianson. Biochemistry 41, 1732 (2002). (http://dx.doi.org/10.1021/bi011960g)
• 30d. M. J. Rynkiewicz, D. E. Cane, D. W. Christianson. Proc. Natl. Acad. Sci. USA 98, 13543 (2001). (http://dx.doi.org/10.1073/pnas.231313098)
• 30e. D. E. Cane. Pure. Appl. Chem. 61, 493 (1989). (http://dx.doi.org/10.1351/pac198961030493)
• 31a. Y. J. Hong, D. J. Tantillo. Org. Lett. 8, 4601 (2006). (http://dx.doi.org/10.1021/ol061884f)
• 31b. Y. J. Hong, D. J. Tantillo. Org. Biomol. Chem. 7, 4101 (2009). (http://dx.doi.org/10.1039/b908738a)
• 32. L. Sun, K. Song, W. L. Hase. Science 296, 875 (2002). (http://dx.doi.org/10.1126/science.1068053)
• 33. S. C. Ammal, H. Yamataka, M. Aida, M. Dupuis. Science 299, 1555 (2003). (http://dx.doi.org/10.1126/science.1079491)