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Volumn 49, Issue 12, 2008, Pages 1943-1947

Total synthesis of mycestericin A

Author keywords

Immunosuppressant; Mycestericin A; Negishi coupling; Overman rearrangement; Total synthesis

Indexed keywords

CARBON; IMMUNOSUPPRESSIVE AGENT; MYCESTERICIN A; NITROGEN; TARTARIC ACID; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG; VINYL CHLORIDE;

EID: 39149126391     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.105     Document Type: Article
Times cited : (21)

References (55)
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    • (1995) Tetrahedron , vol.51 , pp. 6209-6228
  • 20
    • 0037152578 scopus 로고    scopus 로고
    • Tetrahedron 58 (2002) 8779-8791
    • (2002) Tetrahedron , vol.58 , pp. 8779-8791
  • 22
  • 24
    • 39149108242 scopus 로고    scopus 로고
    • Ref. 3h.
    • Ref. 3h.
  • 32
    • 33646064214 scopus 로고    scopus 로고
    • For an excellent review on Overman rearrangement and related reactions, see:. Overman L.E. (Ed), Wiley, New York, NY
    • For an excellent review on Overman rearrangement and related reactions, see:. Overman L.E., and Carpenter N.E. In: Overman L.E. (Ed). Organic Reactions Vol. 66 (2005), Wiley, New York, NY 1-107
    • (2005) Organic Reactions , vol.66 , pp. 1-107
    • Overman, L.E.1    Carpenter, N.E.2
  • 34
    • 39149128403 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR, and mass spectrometric and/or elemental analyses.
  • 36
    • 39149124936 scopus 로고    scopus 로고
    • note
    • The optical purities of 10, 3a, and 3b were all determined to be >99% ee, by a chiral column analysis (Chiralcel OD-H), confirming that no racemization had occurred during the preparation of these compounds.
  • 50
    • 39149141152 scopus 로고    scopus 로고
    • The attempted B-alkyl Suzuki-Miyaura coupling between an alkylborane prepared by the hydroboration of 22 with 9-BBN and 15 gave no coupling product.
    • The attempted B-alkyl Suzuki-Miyaura coupling between an alkylborane prepared by the hydroboration of 22 with 9-BBN and 15 gave no coupling product.
  • 51
    • 39149144617 scopus 로고    scopus 로고
    • The structure of 24 has been tentatively assigned; there is a possibility that compound 24 would be a positional isomer of the conjugated carbon-carbon double bonds.
    • The structure of 24 has been tentatively assigned; there is a possibility that compound 24 would be a positional isomer of the conjugated carbon-carbon double bonds.
  • 54
    • 39149142646 scopus 로고    scopus 로고
    • 4NF in THF or CsF in HMPA.
    • 4NF in THF or CsF in HMPA.
  • 55
    • 39149123935 scopus 로고    scopus 로고
    • note
    • The moderate yield of this step was mainly due to the decomposition of the substrate; the formation of polar by-products, whose structures could not be determined, was observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.