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Volumn 12, Issue 4, 2010, Pages 672-675

Formal synthesis of belactosin A and hormaomycin via a diastereoselective intramolecular cyclopropanation of an α-nitro diazoester

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; BELACTOSIN A; BIOLOGICAL PRODUCT; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; DEPSIPEPTIDE; DRUG DERIVATIVE; HORMAOMYCIN; PEPTIDE;

EID: 76849105966     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol9026528     Document Type: Article
Times cited : (41)

References (42)
  • 4
    • 36849035784 scopus 로고    scopus 로고
    • For recent reviews on 1-aminocyclopropanecarboxylic acids, see: (a) Brackmann, F.; de Meijere, A. Chem, Rev. 2007, 107, 4493-4537.
    • (2007) Chem, Rev. , vol.107 , pp. 4493-4537
    • Brackmann, F.1    De Meijere, A.2
  • 10
    • 76849092590 scopus 로고    scopus 로고
    • Christmann, M., Braese, S., Eds.; Wiley-VCH: Weinheim, and references therein
    • For the synthesis of 1 and 3, see: (a) de Meijere, A.; Larionov, O. V. In Asymmetric Synthesis The Essentials; Christmann, M., Braese, S., Eds.; Wiley-VCH: Weinheim, 2007; pp 67-7.1 and references therein,
    • (2007) Asymmetric Synthesis the Essentials , pp. 67-71
    • De Meijere, A.1    Larionov, O.V.2
  • 22
    • 76849099112 scopus 로고    scopus 로고
    • de Meijere et al. have reported an elegant synthesis of 4 using the separation of two diastereoisomers obtained from an asymmetric alkylation reaction on a racemic mixture of nitrocyclopropanes: ref 7b
    • de Meijere et al. have reported an elegant synthesis of 4 using the separation of two diastereoisomers obtained from an asymmetric alkylation reaction on a racemic mixture of nitrocyclopropanes: ref 7b.
  • 32
    • 0037163295 scopus 로고    scopus 로고
    • For previously reported reaction on 5a, see: Snider, B. B.; Che, Q. Tetrahedron 2002, 58, 7821-7827.
    • (2002) Tetrahedron , vol.58 , pp. 7821-7827
    • Snider, B.B.1    Che, Q.2
  • 37
    • 76849099696 scopus 로고    scopus 로고
    • Erosion, of the ee (from 97 to 53% ee) for compound 9 was observed in the first unoptimized Mitsunobu reaction attempts
    • Erosion, of the ee (from 97 to 53% ee) for compound 9 was observed in the first unoptimized Mitsunobu reaction attempts.
  • 38
    • 76849104288 scopus 로고    scopus 로고
    • -NSuc. and -OTBS substituted diazoesters generated poor diastereoselectivities (3:1 and 1:1, respectively) along with moderate yields. Iodonium ylide cyclopropanation of 11 afforded 15a in 51% yield
    • -NSuc. and -OTBS substituted diazoesters generated poor diastereoselectivities (3:1 and 1:1, respectively) along with moderate yields. Iodonium ylide cyclopropanation of 11 afforded 15a in 51% yield.
  • 39
    • 76849113599 scopus 로고    scopus 로고
    • See Supporting Information for NOESY experiment on the relative configurations of 18 and X-Ray details of 19
    • See Supporting Information for NOESY experiment on the relative configurations of 18 and X-Ray details of 19.
  • 40
    • 76849103908 scopus 로고    scopus 로고
    • Ensuing steps to the oxidation of 19 using methylester derivatives afforded the corresponding deprotected acid along with cyclopropane opening by-products
    • Ensuing steps to the oxidation of 19 using methylester derivatives afforded the corresponding deprotected acid along with cyclopropane opening by-products.
  • 41
    • 76849111198 scopus 로고    scopus 로고
    • See Supporting Information for NOESY experiment on the relative configuration of 22
    • See Supporting Information for NOESY experiment on the relative configuration of 22.
  • 42
    • 76849111537 scopus 로고    scopus 로고
    • References 5b and 7b reported the synthesis of protected (AcP) and (NcP)Ala in 16% yield over 8 steps and 13% yield over 6 steps, respectively
    • References 5b and 7b reported the synthesis of protected (AcP) and (NcP)Ala in 16% yield over 8 steps and 13% yield over 6 steps, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.