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Volumn 10, Issue 23, 2008, Pages 5457-5460

Total synthesis of (-)-agelastatin A

Author keywords

[No Author keywords available]

Indexed keywords

AGELASTATIN A; ALKALOID; IMIDAZOLE; IMIDAZOLE DERIVATIVE; KETONE; LACTAM; NITROGEN; OXAZOLIDINONE DERIVATIVE;

EID: 61349122654     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802225g     Document Type: Article
Times cited : (68)

References (61)
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    • Studies on the biological activity of agelastatin A: (a) Mason, C. K.; McFarlane, S.; Johnston, P. G.; Crowe, P.; Erwin, P. J.; Domostoj, M. M.; Campbell, F. C.; Manaviazar, S.; Hale, K. J.; El-Tanani, M. Mol. Cancer Ther. 2008, 7, 548.
    • Studies on the biological activity of agelastatin A: (a) Mason, C. K.; McFarlane, S.; Johnston, P. G.; Crowe, P.; Erwin, P. J.; Domostoj, M. M.; Campbell, F. C.; Manaviazar, S.; Hale, K. J.; El-Tanani, M. Mol. Cancer Ther. 2008, 7, 548.
  • 8
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    • Synthetic studies on the potent anticancer natural compounds from this laboratory: (a) Yoshimitsu, T.; Sasaki, S.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2004, 69, 9262.
    • Synthetic studies on the potent anticancer natural compounds from this laboratory: (a) Yoshimitsu, T.; Sasaki, S.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2004, 69, 9262.
  • 12
    • 0032582593 scopus 로고    scopus 로고
    • Total and formal syntheses of agelastatin A: (a) Anderson, G. T.; Chase, C. E.; Koh, Y.-H.; Stien, D.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1998, 63, 7594.
    • Total and formal syntheses of agelastatin A: (a) Anderson, G. T.; Chase, C. E.; Koh, Y.-H.; Stien, D.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1998, 63, 7594.
  • 29
    • 29544440346 scopus 로고    scopus 로고
    • This is also known as the Clauson-Kaas pyrrole synthesis: (a) Gourlay, B. S, Molesworth, P. P, Ryan, J. H, Smith. J. A. Tetrahedron Lett. 2006, 47, 799
    • This is also known as the Clauson-Kaas pyrrole synthesis: (a) Gourlay, B. S.; Molesworth, P. P.; Ryan, J. H.; Smith. J. A. Tetrahedron Lett. 2006, 47, 799.
  • 32
    • 29344457003 scopus 로고    scopus 로고
    • For recent reviews on catalytic aziridination chemistry using azides, see: a
    • For recent reviews on catalytic aziridination chemistry using azides, see: (a) Katsuki, T. Chem. Lett. 2005, 34, 1304.
    • (2005) Chem. Lett , vol.34 , pp. 1304
    • Katsuki, T.1
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    • It is also likely that water hydrolyzes TMS-imidazole that is possibly generated by the reaction of carbonyl imidazolide with TMSN3 and readily undergoes addition to azidoformate 5
    • 3 and readily undergoes addition to azidoformate 5.
  • 35
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    • Thermolysis and related reactions of azidoformates leading to aziridination: (a) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1999, 64, 2852.
    • Thermolysis and related reactions of azidoformates leading to aziridination: (a) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1999, 64, 2852.
  • 42
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    • This aziridination under photolytic conditions, however, furnished only a low yield (ca. 10, of aziridine 4. For the photolysis of azidoformates, see: (a) Mendlik, M. T, Tao, P, Hadad, C. M, Coleman, R. S, Lowary, T. L. J. Org. Chem. 2006, 71, 8059
    • This aziridination under photolytic conditions, however, furnished only a low yield (ca. 10%) of aziridine 4. For the photolysis of azidoformates, see: (a) Mendlik, M. T.; Tao, P.; Hadad, C. M.; Coleman, R. S.; Lowary, T. L. J. Org. Chem. 2006, 71, 8059.
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    • For a review, see: p
    • For a review, see: (p) Hu, X. E. Tetrahedron 2004, 60, 2701.
    • (2004) Tetrahedron , vol.60 , pp. 2701
    • Hu, X.E.1
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    • 2 to the oxazolidinone carbonyl group of the Boc-protected intermediate SI-3. followed by cyclization of the resultant Boc-protected urea i. (Chemical Equation Presented)
    • 2 to the oxazolidinone carbonyl group of the Boc-protected intermediate SI-3. followed by cyclization of the resultant Boc-protected urea i. (Chemical Equation Presented)
  • 61
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    • The compound 17 is somewhat unstable under the present oxidation conditions, probably due to the susceptibility to facile elimination of the pyrrole group from the ketone intermediate.
    • The compound 17 is somewhat unstable under the present oxidation conditions, probably due to the susceptibility to facile elimination of the pyrrole group from the ketone intermediate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.