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Volumn 121, Issue 41, 1999, Pages 9574-9579

Total synthesis of the antitumor marine sponge alkaloid agelastatin A

Author keywords

[No Author keywords available]

Indexed keywords

AGELASTATIN A; ALKALOID; ANTINEOPLASTIC AGENT; CARBAMIC ACID; CYCLOPENTADIENE DERIVATIVE; ISOCYANATE; KETONE; UNCLASSIFIED DRUG;

EID: 0032748434     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992487l     Document Type: Article
Times cited : (115)

References (40)
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    • (c) Weinreb, S. M. Heterodienophile Additions to Dienes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 401.
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    • For some other syntheses of oxazolidinone 11, see: Mulvihill, M. J.; Gage, J. L.; Miller, M. J. J. Org. Chem. 1998, 63, 3357. Muxworthy, J. P.; Wilkinson, J. A.; Procter, G. Tetrahedron Lett. 1995, 36, 7539.
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    • Mulvihill, M.J.1    Gage, J.L.2    Miller, M.J.3
  • 13
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    • For some other syntheses of oxazolidinone 11, see: Mulvihill, M. J.; Gage, J. L.; Miller, M. J. J. Org. Chem. 1998, 63, 3357. Muxworthy, J. P.; Wilkinson, J. A.; Procter, G. Tetrahedron Lett. 1995, 36, 7539.
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  • 19
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    • We thank Dr. M. Shang (University of Notre Dame) for this analysis. X-ray data for this compound can be found in the Supporting Information for ref 3.
    • We thank Dr. M. Shang (University of Notre Dame) for this analysis. X-ray data for this compound can be found in the Supporting Information for ref 3.
  • 21
    • 0032555006 scopus 로고    scopus 로고
    • For formation of π-allylpalladium complexes from oxazolidinones, see: Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 3405. Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3405
    • Cook, G.R.1    Shanker, P.S.2
  • 22
    • 0032499973 scopus 로고    scopus 로고
    • For formation of π-allylpalladium complexes from oxazolidinones, see: Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 3405. Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4991
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    • Electrophilic Heteroatom Cyclizations
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    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 363
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    • See, for example: Backvall, J.-E.; Andersson, P. G. J. Am. Chem. Soc. 1990, 112, 3683. Andersson, P. G.; Aranyos, A. Tetrahedron Lett. 1994, 55, 4441.
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    • note
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    • note
    • The presence of a substituent at C-5a is important, however, since LiOH hydrolysis of the unsubstituted system 13 affords a 2:1 ratio of Boc cleavage product 11 to the product of cleavage of the cyclic carbamate.
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    • Jung, M. E.; Lyster, M. A. J. Chem. Soc., Chem. Commun. 1978, 315. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495. Cf. also: Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543.
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    • Jung, M. E.; Lyster, M. A. J. Chem. Soc., Chem. Commun. 1978, 315. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495. Cf. also: Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543.
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