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Volumn 7, Issue 5, 2005, Pages 823-826

DYKAT of vinyl aziridines: Total synthesis of (+)-pseudodistomin D

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ANTINEOPLASTIC AGENT; AZIRIDINE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; PIPERIDINE; PSEUDODISTOMIN D; SILVER; UNCLASSIFIED DRUG; VINYLAZIRIDINE;

EID: 15044351640     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047513l     Document Type: Article
Times cited : (86)

References (47)
  • 27
  • 33
    • 15044361299 scopus 로고    scopus 로고
    • note
    • Ohira - Bestmann reagent = dimethyl(acetyldia/omethyl)phosphonate.
  • 42
    • 15044344182 scopus 로고    scopus 로고
    • note
    • 3CN afforded complete decomposition in 10 min at 60 C. No competitive decomposition was observed under analogous hydroamination conditions with undec-5-ynylamine.
  • 43
    • 15044347727 scopus 로고    scopus 로고
    • note
    • Using a more standard strategy in which the appropriate ketodiamine undergoes an intramolecular reductive animation, the pyrrolidine and/or piperidine products were obtained in modest yields. Given the additional steps necessary to furnish the keto-diamine and the modest yield of the subsequent reductive animation, this strategy was disfavored over the reductive hydroamination reported herein. By both chromatographic and spectroscopic methods, the pyrrolidine and piperidine are easily distinguishable.
  • 45
    • 0036134113 scopus 로고    scopus 로고
    • Examples of six-membered imine reduction occurring selectively over five-membered imine reduction in an approach toward thiostrepton are: (a) Higashibayashi, S.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2002, 43, 105-110. (b) Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.: Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941-1945.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 105-110
    • Higashibayashi, S.1    Hashimoto, K.2    Nakata, M.3
  • 46
    • 0037014040 scopus 로고    scopus 로고
    • Examples of six-membered imine reduction occurring selectively over five-membered imine reduction in an approach toward thiostrepton are: (a) Higashibayashi, S.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2002, 43, 105-110. (b) Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.: Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941-1945.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1941-1945
    • Nicolaou, K.C.1    Nevalainen, M.2    Safina, B.S.3    Zak, M.4    Bulat, S.5
  • 47
    • 0038762733 scopus 로고    scopus 로고
    • Wave Function, Inc.: Irivine, CA
    • Semiempirical PM3 calculations indicate that the equilibrium favors imine 16 over imine 14 by 3-7 kcal/mol. Spartan '02; Wave Function, Inc.: Irivine, CA, 2002.
    • (2002) Spartan '02


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.