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Volumn 127, Issue 32, 2005, Pages 11505-11515

Total synthesis of (-)-spirotryprostatin B: Synthesis and related studies

Author keywords

[No Author keywords available]

Indexed keywords

MAGNESIUM COMPOUNDS; OLEFINS; ORGANIC COMPOUNDS;

EID: 23844449033     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0518880     Document Type: Article
Times cited : (309)

References (97)
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    • note
    • 1H NMR and high-resolution MALDI-MS), resulting from quenching of 7 with water in a reaction wherein the imine decomposed.
  • 17
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    • The ring closure of iminium (pathway A) is a disfavored 5-endo-trig cyclization process: (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736.
    • (1976) J. Chem. Soc., Chem. Commun. , pp. 734-736
    • Baldwin, J.E.1
  • 28
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    • A couple of examples for disfavored 5-endo-trig cyclization reactions are known in the literature for the formation of tetrahydrofuranes: (a) Craig, D.; Smith, A. M. Tetrahedron Lett. 1992, 33, 695-698.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 695-698
    • Craig, D.1    Smith, A.M.2
  • 38
    • 33645390737 scopus 로고    scopus 로고
    • CCDC 199469 and CCDC 199470 contain the supplementary crystallographic data for 16 and 17 respectively. These data can be obtained free of charge via www.ccdc.cam.ac.uk/retrieving.html (or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB21EZ, U.K.; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 41
    • 33645393323 scopus 로고    scopus 로고
    • note
    • For preparation of the cyclopropyl derivatives 19-23, see Supporting Information.
  • 42
    • 33645384341 scopus 로고    scopus 로고
    • note
    • A simplification of the starting materials (R″ = H) requires the implementation of the C8-C9 olefin without the installation of a masked leaving group, a problem already solved in Danishefsky's synthesis of spirotryprostatin B (see ref 7).
  • 47
    • 18444417883 scopus 로고
    • For recent reviews see: (d) Doyle, M. P. Chem. Rev. 1986, 86, 919-939.
    • (1986) Chem. Rev. , vol.86 , pp. 919-939
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  • 51
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    • (These findings were confirmed by Davies: Davies, H. M. L.; Clark, T. J.; Smith, H. D. J. Org. Chem. 1991, 56, 3817-3824.) In the case of 2-substituted dienes, electronic factors associated with changes in the electrophilicities of the reactant metal carbenes proved relevant.
    • (1991) J. Org. Chem. , vol.56 , pp. 3817-3824
    • Davies, H.M.L.1    Clark, T.J.2    Smith, H.D.3
  • 57
    • 0001676855 scopus 로고
    • Isomerization of the spirocenter of oxindoles is widely known and is proposed to occur via a retro-Mannich reaction see: (a) Wenkert, E.; Udelhofen, J. H.; Bhattacharyya, N. K. J. Am. Chem. Soc. 1959, 81, 3763-3768.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 3763-3768
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    • CCDC 196803 contains the supplementary crystallographic data for 46. These data can be obtained free of charge via www.ccdc.cam.ac.uk/retrieving.html (or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB21EZ, U.K.; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
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    • 4-promoted catalytic oxidative cleavage was tested, but only traces of the desired material was obtained, making this direct method incompatible with the traditional three-step sequence. Travis, B. R.; Narayan, R. S.; Borhan, B. J. Am. Chem. Sac. 2002, 124, 3824-3825.
    • (2002) J. Am. Chem. Sac. , vol.124 , pp. 3824-3825
    • Travis, B.R.1    Narayan, R.S.2    Borhan, B.3
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    • 2 was prepared from N-methyl-N′-nitro-N- nitrosoguanidine and was used as an ethereal solution. Fales, H. M.; Jaouni, T. M.; Babashak, J. F. Anal. Chem. 1973, 45, 2302-2303.
    • (1973) Anal. Chem. , vol.45 , pp. 2302-2303
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  • 73
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    • 3/PbO) in the experimental part. (c) Initial trials were undertaken using Lindlar's catalyst; however, only recovered starting material 52 was isolated under standard conditions. Lindlar, H. Helv. Chim. Acta 1952, 35, 446-456.
    • (1952) Helv. Chim. Acta , vol.35 , pp. 446-456
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    • CCDC 196804 contains the supplementary crystallographic data for 59 These data can be obtained free of charge via www.ccdc.cam.ac.uk/retrieving.html (or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB21EZ, U.K.; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.