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Volumn 69, Issue 21, 2004, Pages 7309-7316

Mitomycin synthetic studies: Stereocontrolled and convergent synthesis of a fully elaborated aziridinomitosane

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ANALYSIS; MOLECULAR DYNAMICS; SYNTHESIS (CHEMICAL);

EID: 5444237056     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048924i     Document Type: Article
Times cited : (45)

References (49)
  • 4
    • 0001111750 scopus 로고
    • Mitomycins and porfiromycin
    • Wiley-Interscience: New York
    • Remers, W. A. Mitomycins and porfiromycin. In The Chemistry of Antitumor Antibiotics; Wiley-Interscience: New York, 1979; pp 221-276.
    • (1979) The Chemistry of Antitumor Antibiotics , pp. 221-276
    • Remers, W.A.1
  • 12
    • 0001128802 scopus 로고
    • Total synthesis of mitomycins
    • Atta-ur-Rahman, Ed.; Elsevier: New York
    • (c) Fukuyama, T.; Yang, L. Total Synthesis of Mitomycins. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1993; pp 433-471.
    • (1993) Studies in Natural Products Chemistry , pp. 433-471
    • Fukuyama, T.1    Yang, L.2
  • 14
    • 5444226915 scopus 로고
    • (b) For a review of work from the Kishi group, see: Kishi, Y. J. Nat. Prod. 1979, 42, 9388.
    • (1979) J. Nat. Prod. , vol.42 , pp. 9388
    • Kishi, Y.1
  • 28
    • 0002387069 scopus 로고
    • The addition and substitution chemistry of quinones
    • Patai, S., Ed., Wiley: New York
    • Finley, K. T. The addition and substitution chemistry of quinones. In Chemistry of the Quinonoid Compounds; Patai, S., Ed., Wiley: New York, 1974; Vol. 2, pp 877-1144.
    • (1974) Chemistry of the Quinonoid Compounds , vol.2 , pp. 877-1144
    • Finley, K.T.1
  • 42
    • 0034831037 scopus 로고    scopus 로고
    • and references therein
    • Fleming, I. Chemtracts 2001, 14, 405 and references therein.
    • (2001) Chemtracts , vol.14 , pp. 405
    • Fleming, I.1
  • 45
    • 5444250285 scopus 로고    scopus 로고
    • note
    • 1H NMR and HRMS (ESI). The MS data confirmed the molecular formula and allowed at least some NMR assignments to be made. We found it essentially impossible to confirm the identity of reaction products using NMR as the sole method of characterization.
  • 46
    • 5444275585 scopus 로고    scopus 로고
    • note
    • 2O, 25 °C, 87%] to afford the quinone 48, thereby validating the feasibility of maintaining the integrity of the aziridine ring system through this reaction sequence. (Diagram presented)
  • 47
    • 5444255451 scopus 로고    scopus 로고
    • note
    • It proved impossible to remove a pyrrolidine tert-butyl carbamate once the C10 carbamate and/or the quinone were installed; intermediates possessing a benzyl carbamate protecting the pyrrolidine nitrogen could be converted to a quinone bearing system.
  • 49
    • 5444267838 scopus 로고    scopus 로고
    • note
    • Comparable syntheses of 1 or a closely related compound have required 32 total steps (20 linear)13a or 27 steps (27 linear).13b


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.