Synthetic studies on the ingenane diterpenes. Direct conversion of the out,out-bicyclo[4.4.1]undecane system into a highly strained in,out stereoisomer

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 7992-7993

  Rigby, James H ^a   De Sainte Claire, Valérie ^a   Cuisiat, Stephane V ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[4.4.1]UNDECANE DERIVATIVE; DITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029824760     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961714o     Document Type: Article

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10. For recent work on other in,out-bridged bicycloalkanes, see: (a) Adler, R. W. Acc. Chem. Res. 1983, 16, 321. (b) Kato, T.; Hirukawa, T.; Uyehara, T.; Yamamoto, Y. Tetrahedron Lett. 1987, 28, 1439. (c) Winkler, J. D.; Hey, J. P.; Williard, P. G. J. Am. Chem. Soc. 1986, 108, 6425. (d) McMurry, J. E.; Hodge, C. N. J. Am. Chem. Soc. 1984, 106, 6450. (e) Gassman, P. G.; Hoye, R. C. J. Am. Chem. Soc. 1981, 103, 2496.
11. For recent work on other in,out-bridged bicycloalkanes, see: (a) Adler, R. W. Acc. Chem. Res. 1983, 16, 321. (b) Kato, T.; Hirukawa, T.; Uyehara, T.; Yamamoto, Y. Tetrahedron Lett. 1987, 28, 1439. (c) Winkler, J. D.; Hey, J. P.; Williard, P. G. J. Am. Chem. Soc. 1986, 108, 6425. (d) McMurry, J. E.; Hodge, C. N. J. Am. Chem. Soc. 1984, 106, 6450. (e) Gassman, P. G.; Hoye, R. C. J. Am. Chem. Soc. 1981, 103, 2496.
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19. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
20. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
21. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
22. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
23. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
24. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
25. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
26. For recent approaches to 8-isoingenol, possessing the out,out intrabridgehead stereochemistry, see: (a) Paquette, L. A.; Nitz, T. J.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 1446. (b) Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398. (c) Funk, R. L.; Bolton, G. L. J. Am. Chem. Soc. 1986, 108, 4655. (d) Ross, R. J.; Paquette, L. A. J. Org. Chem. 1987, 52, 5497. (e) Mehta, G.; Pathak, V. P. J. Chem. Soc., Chem. Commun. 1987, 876. (f) Paquette, L. A.; Ross, R. J.; Springer, J. P. J. Am. Chem. Soc. 1988, 110, 6192. (g) Rigby, J. H.; Cuisiat, S. V. J. Org. Chem. 1993, 58, 6286. (h) Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
27. 7a
28. (a) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579.
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31. 13C NMR, IR) and analytical (combustion analysis and/or HRMS) data fully consistent with the assigned structure.
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36. The structure of this compound was determined by single-crystal X-ray analysis.
37. The neutral version of this rearrangement has been shown to proceed in a suprafacial fashion: Eggert, U.; Stohrer, I.; Hoffmann, H. M. R. Tetrahedron Lett. 1992, 33, 3465.
38. Rigby, J. H.; Moore, T. L. J. Org. Chem. 1990, 55, 2959.
39. The author has deposited atomic coordinates for 7 and 8 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.