A Convergent Synthesis of the Tricyclic Architecture of the Guanacastepenes Featuring a Selective Ring Fragmentation

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2063-2066

  Shipe, William D ^a   Sorensen, Erik J ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; GUANACASTEPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

DITERPENES; MOLECULAR STRUCTURE;

EID: 0037071924     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0259342     Document Type: Article

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23. For examples of selective cyclobutyl bond cleavages, see: (a) Crimmins M. T.; Mascarella, S. W. Tetrahedron Lett. 1987, 28, 5063-5066. (b) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418. (c) Cossy, J.; Aclinou, P.; Bellosta, V.; Furet, N.; Baranne-Lafont, J.; Spartel, D.; Souchaud, C. Tetrahedron Lett. 1991, 32, 1315-1316. (d) Crimmins, M. T.; Dudek, C. M.; Cheung, A. W.-H. Tetrahedron Lett. 1992, 33, 181-184. (e) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. Tetrahedron Lett. 1996, 37, 8703-8706. (f) Ziegler, F. E.; Kover, R. X.; Yee, N. N. K. Tetrahedron Lett. 2000, 41, 5155-5159.
24. For examples of selective cyclobutyl bond cleavages, see: (a) Crimmins M. T.; Mascarella, S. W. Tetrahedron Lett. 1987, 28, 5063-5066. (b) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418. (c) Cossy, J.; Aclinou, P.; Bellosta, V.; Furet, N.; Baranne-Lafont, J.; Spartel, D.; Souchaud, C. Tetrahedron Lett. 1991, 32, 1315-1316. (d) Crimmins, M. T.; Dudek, C. M.; Cheung, A. W.-H. Tetrahedron Lett. 1992, 33, 181-184. (e) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. Tetrahedron Lett. 1996, 37, 8703-8706. (f) Ziegler, F. E.; Kover, R. X.; Yee, N. N. K. Tetrahedron Lett. 2000, 41, 5155-5159.
25. For examples of selective cyclobutyl bond cleavages, see: (a) Crimmins M. T.; Mascarella, S. W. Tetrahedron Lett. 1987, 28, 5063-5066. (b) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418. (c) Cossy, J.; Aclinou, P.; Bellosta, V.; Furet, N.; Baranne-Lafont, J.; Spartel, D.; Souchaud, C. Tetrahedron Lett. 1991, 32, 1315-1316. (d) Crimmins, M. T.; Dudek, C. M.; Cheung, A. W.-H. Tetrahedron Lett. 1992, 33, 181-184. (e) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. Tetrahedron Lett. 1996, 37, 8703-8706. (f) Ziegler, F. E.; Kover, R. X.; Yee, N. N. K. Tetrahedron Lett. 2000, 41, 5155-5159.
26. For examples of selective cyclopropyl bond cleavages, see: (a) Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945-4947. (b) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431. (c) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652. (d) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220. (e) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418.
27. For examples of selective cyclopropyl bond cleavages, see: (a) Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945-4947. (b) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431. (c) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652. (d) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220. (e) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418.
28. For examples of selective cyclopropyl bond cleavages, see: (a) Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945-4947. (b) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431. (c) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652. (d) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220. (e) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418.
29. For examples of selective cyclopropyl bond cleavages, see: (a) Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945-4947. (b) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431. (c) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652. (d) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220. (e) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418.
30. For examples of selective cyclopropyl bond cleavages, see: (a) Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945-4947. (b) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431. (c) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649-6652. (d) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220. (e) Ziegler, F. E.; Zheng, Z. J. Org. Chem. 1990, 55, 1416-1418.
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43. 2O with silica gel results in the formation of 24. The structure of 24 is supported by gHMBC, gHSQC, gdqCOSY, and ROESY experiments.
44. Attempts to add the dioxolane-protected cyclopentenyllithium to 26 using various protocols were unsuccessful.
45. Examination of molecular models indicates that 29 is not contormationally inclined to undergo [2 + 2] photocycloaddition. However the epimer giving rise to 30 can easily access the necessary alignment for cycloaddition.