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Volumn 65, Issue 15, 2000, Pages 4685-4693

A biomimetic total synthesis of (-)-spirotryprostatin B and related studies

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PIPERAZINEDIONE; SPIROTRYPROSTATIN B; UNCLASSIFIED DRUG;

EID: 0034725771     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000306o     Document Type: Article
Times cited : (117)

References (42)
  • 2
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    • For a review of earlier synthetic efforts, see: Hino, T.; Nakagawa, M. Heterocycles 1997, 46, 673-704.
    • (1997) Heterocycles , vol.46 , pp. 673-704
    • Hino, T.1    Nakagawa, M.2
  • 10
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    • note
    • Abbreviations: APCI = atmospheric pressure chemical ionization; ESI = electrospray ionization; Fmoc = (9H-fluoren-9-ylmethoxy)-carbonyi; HMQC = heteronuclear multiple quantum correlation spectroscopy; HMBC = heteronuclear multiple bond correlation spectroscopy; Trp = tryptophan; Pro = proline.
  • 11
    • 0343559109 scopus 로고    scopus 로고
    • note
    • The L-Trp-L-Pro diketopiperazine is itself a fungal natural product, brevianamide F.
  • 15
    • 0032939472 scopus 로고    scopus 로고
    • For an interesting nonbiomimetic route to oxindoles via 1,3-dipolar cycloaddition of azomethine ylides, see: Nyerges, M.; Gajdics, L.; Szöllösy, A.; Töke, L. Synlett 1999, 111-113.
    • (1999) Synlett , pp. 111-113
    • Nyerges, M.1    Gajdics, L.2    Szöllösy, A.3    Töke, L.4
  • 25
    • 0011448791 scopus 로고    scopus 로고
    • Las Vegas, 7-11 Sep 1997, abstract ORGN 282
    • The synthesis of 7 was presented at the 214th ACS National Meeting, Las Vegas, 7-11 Sep 1997, abstract ORGN 282.
    • 214th ACS National Meeting
  • 29
    • 0342688876 scopus 로고    scopus 로고
    • note
    • (b) See also ref 12 and 19.
  • 32
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    • note
    • 2H).
  • 36
    • 0015538314 scopus 로고
    • Similar diketopiperazine iminium ions have been invoked, for example, with thio-subsituted Pro-Pro derivatives, as well as the chemistry of bicyclomycin and related bridgehead compounds: (a) Öhler, E.; Tataruch, F.; Schmidt, U. Chem. Ber. 1973, 106, 165-176. (b) Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Am. Chem. Soc. 1985, 107, 3253-3260. (c) Williams, R. M.; Dung, J.-S. Tetrahedron Lett. 1985, 26, 37-38.
    • (1973) Chem. Ber. , vol.106 , pp. 165-176
    • Öhler, E.1    Tataruch, F.2    Schmidt, U.3
  • 37
    • 0021952743 scopus 로고
    • Similar diketopiperazine iminium ions have been invoked, for example, with thio-subsituted Pro-Pro derivatives, as well as the chemistry of bicyclomycin and related bridgehead compounds: (a) Öhler, E.; Tataruch, F.; Schmidt, U. Chem. Ber. 1973, 106, 165-176. (b) Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Am. Chem. Soc. 1985, 107, 3253-3260. (c) Williams, R. M.; Dung, J.-S. Tetrahedron Lett. 1985, 26, 37-38.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3253-3260
    • Williams, R.M.1    Armstrong, R.W.2    Dung, J.-S.3
  • 38
    • 0343995261 scopus 로고
    • Similar diketopiperazine iminium ions have been invoked, for example, with thio-subsituted Pro-Pro derivatives, as well as the chemistry of bicyclomycin and related bridgehead compounds: (a) Öhler, E.; Tataruch, F.; Schmidt, U. Chem. Ber. 1973, 106, 165-176. (b) Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Am. Chem. Soc. 1985, 107, 3253-3260. (c) Williams, R. M.; Dung, J.-S. Tetrahedron Lett. 1985, 26, 37-38.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 37-38
    • Williams, R.M.1    Dung, J.-S.2
  • 39
    • 0032143275 scopus 로고    scopus 로고
    • These assays were performed by Professor Osada's group, according to published methods, ref 3, and: (a) Usui, T.; Kondoh, M.; Cui, C.-B.; Mayumi, T.; Osada, H. Biochem. J. 1998, 333, 543-548. (b) Kondoh, M.; Usui, T.; Mayumi, T.; Osada, H. J. Antibiot. 1998, 5, 801-804.
    • (1998) Biochem. J. , vol.333 , pp. 543-548
    • Usui, T.1    Kondoh, M.2    Cui, C.-B.3    Mayumi, T.4    Osada, H.5
  • 40
    • 0031687689 scopus 로고    scopus 로고
    • These assays were performed by Professor Osada's group, according to published methods, ref 3, and: (a) Usui, T.; Kondoh, M.; Cui, C.-B.; Mayumi, T.; Osada, H. Biochem. J. 1998, 333, 543-548. (b) Kondoh, M.; Usui, T.; Mayumi, T.; Osada, H. J. Antibiot. 1998, 5, 801-804.
    • (1998) J. Antibiot. , vol.5 , pp. 801-804
    • Kondoh, M.1    Usui, T.2    Mayumi, T.3    Osada, H.4
  • 41
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    • note
    • Note Added in Proof. After submission of this paper, we have learned of independent syntheses of 3 by the groups of Danishefsky, Overman, and Williams.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.