Total syntheses of (+)-cylindricines C-E and (-)-lepadiformine through a common intermediate derived from an aza-Prins cyclization and Wharton's rearrangement

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3989-3992

  Liu, Jia ^a   Hsung, Richard P ^a   Peters, Scott D ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYLINDRICINE C; CYLINDRICINE D; CYLINDRICINE E; LEPADIFORMINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; CYCLOADDITION; DRUG SYNTHESIS; REACTION ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

ALKALOIDS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; AZA COMPOUNDS; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 3-RING; QUINOLONES; STEREOISOMERISM;

EID: 8744262719     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048353g     Document Type: Article

References (57)

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38. For some examples of natural product synthesis that employ a tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem. Soc. 1974, 96, 6516. (b) Rykman, D. M.; Stevens, R. V. J. Am. Chem. Soc. 1987, 109, 4940. (c) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164. (d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Heterocycles 1994, 37, 933. (e) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Morita, T.; Kitajima, H. Heterocycles 1996, 43, 71. (f) Scott, R. W.; Epperson, J.; Heathcock, C. H. J. Org. Chem. 1998, 63, 5001.
39. For some examples of natural product synthesis that employ a tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem. Soc. 1974, 96, 6516. (b) Rykman, D. M.; Stevens, R. V. J. Am. Chem. Soc. 1987, 109, 4940. (c) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164. (d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Heterocycles 1994, 37, 933. (e) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Morita, T.; Kitajima, H. Heterocycles 1996, 43, 71. (f) Scott, R. W.; Epperson, J.; Heathcock, C. H. J. Org. Chem. 1998, 63, 5001.
40. For some examples of natural product synthesis that employ a tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem. Soc. 1974, 96, 6516. (b) Rykman, D. M.; Stevens, R. V. J. Am. Chem. Soc. 1987, 109, 4940. (c) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164. (d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Heterocycles 1994, 37, 933. (e) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Morita, T.; Kitajima, H. Heterocycles 1996, 43, 71. (f) Scott, R. W.; Epperson, J.; Heathcock, C. H. J. Org. Chem. 1998, 63, 5001.
41. For some examples of natural product synthesis that employ a tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem. Soc. 1974, 96, 6516. (b) Rykman, D. M.; Stevens, R. V. J. Am. Chem. Soc. 1987, 109, 4940. (c) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164. (d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Heterocycles 1994, 37, 933. (e) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Morita, T.; Kitajima, H. Heterocycles 1996, 43, 71. (f) Scott, R. W.; Epperson, J.; Heathcock, C. H. J. Org. Chem. 1998, 63, 5001.
42. For some examples of natural product synthesis that employ a tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem. Soc. 1974, 96, 6516. (b) Rykman, D. M.; Stevens, R. V. J. Am. Chem. Soc. 1987, 109, 4940. (c) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164. (d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Heterocycles 1994, 37, 933. (e) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Morita, T.; Kitajima, H. Heterocycles 1996, 43, 71. (f) Scott, R. W.; Epperson, J.; Heathcock, C. H. J. Org. Chem. 1998, 63, 5001.
43. For some examples of natural product synthesis that employ a tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem. Soc. 1974, 96, 6516. (b) Rykman, D. M.; Stevens, R. V. J. Am. Chem. Soc. 1987, 109, 4940. (c) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164. (d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Heterocycles 1994, 37, 933. (e) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Morita, T.; Kitajima, H. Heterocycles 1996, 43, 71. (f) Scott, R. W.; Epperson, J.; Heathcock, C. H. J. Org. Chem. 1998, 63, 5001.
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52. Also see: (a) Stork, G., Williard, P. J. Am. Chem. Soc. 1977, 99, 7067. (b) Schult-Elte, K. H.; Rautenstrauch, V.; Ohloff, G. Helv. Chim Acta 1971, 54, 1805. (c) Ohloff, G.; Uhde, G. Helv. Chim Act. 1970, 53, 531.
53. Also see: (a) Stork, G., Williard, P. J. Am. Chem. Soc. 1977, 99, 7067. (b) Schult-Elte, K. H.; Rautenstrauch, V.; Ohloff, G. Helv. Chim Acta 1971, 54, 1805. (c) Ohloff, G.; Uhde, G. Helv. Chim Act. 1970, 53, 531.
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55. D23.
56. We note here that compound 26 actually has the identical characterizations as penultimate intermediate in Trost's synthesis [ref 6]. However, we are comfortable with our assignment of 26 on the basis of the fact that (1) a total synthesis of (-)-lepadiformine was achieved using 26 and (2) desilylation of 26 using TBAF directly gave (+)-cylindricine C concomitant with the C5 epimerization.
57. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.