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Volumn 62, Issue 45, 2006, Pages 10518-10527

Further studies on enantioselective synthesis of (+)-anatoxin-a using enyne metathesis: unexpected inversion of chirality via a skeletal rearrangement of 9-azabicyclo[4.2.1]nonene derivative

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ANATOXIN A; BICYCLO COMPOUND; PYROGLUTAMIC ACID;

EID: 33748985453     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.088     Document Type: Article
Times cited : (23)

References (82)
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    • For a review of the construction of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis, see:
    • For a review of the construction of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis, see:. Deiters A., and Martin S.F. Chem. Rev. 104 (2004) 2199
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    • For a recent review on synthetic approach to anatoxin-a, see:
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    • and references cited therein
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    • For recent reports on the synthesis of (+)- and/or (-)-anatoxin-a, see:
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    • For recent reports on the synthesis of (±)-anatoxin-a, see:
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    • For a preliminary communication of a part of this work, see:. Mori M., Tomita T., Kita Y., and Kitamura T. Tetrahedron Lett. 45 (2004) 4397
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4397
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  • 61
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    • At almost the same time as publication of our synthesis of (+)-anatoxin-a (Ref. 9), Martin et al. reported the synthesis of (+)-anatoxin-a from (R)-(+)-pyroglutamic acid in which enyne metathesis was used for construction of a 9-azabicyclo[4.2.1]nonene skeleton. See:
  • 64
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    • The synthesis of (-)-ferruginine, which has a structure similar to that of anatoxin-a, was recently reported, in which a 7-azabicyclo[3.2.1]octane skeleton was constructed from pyrrolidine derivative using an enyne metathesis. See:
    • The synthesis of (-)-ferruginine, which has a structure similar to that of anatoxin-a, was recently reported, in which a 7-azabicyclo[3.2.1]octane skeleton was constructed from pyrrolidine derivative using an enyne metathesis. See:. Aggarwal V.K., Astle C.J., and Rogers-Evans M. Org. Lett. 6 (2004) 1469
    • (2004) Org. Lett. , vol.6 , pp. 1469
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    • For a lead reference to the discussion on the role of ethylene gas in enyne metathesis, see:. Lloyd-Jones G.C., Margue R.G., and de Varies J.G. Angew. Chem., Int. Ed. 44 (2005) 7442
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7442
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    • For other examples of intermolecular metathesis of alkyne and ethylene, see:
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    • note
    • In the metathesis of enyne having a silyl group on the alkyne, desilylation did not usually occur. See Ref. 4p.
  • 80
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    • note
    • The optical purity of the recovered 4a was completely same to that of the starting material 4a of the oxymercuration reaction.
  • 81
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    • note
    • 9 the structure of the synthetic (+)-N-Ts-anatoxin-a was incorrectly drawn as that of the antipode (i.e., (-)-N-Ts-anatoxin-a) because of the confusion arising from the unexpected inversion of chirality.
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    • note
    • Crystallographic data for the structure of 18 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 295170. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.