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Volumn 74, Issue 1, 2009, Pages 423-426

Direct oxa-Pictet-Spengler cyclization to the natural (3a,5)-trans- stereochemistry in the syntheses of (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIASTEREO SELECTIVITIES;

EID: 58149305978     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801945n     Document Type: Article
Times cited : (39)

References (25)
  • 2
    • 58149314643 scopus 로고    scopus 로고
    • Unpublished results
    • Unpublished results.
  • 9
    • 58149294093 scopus 로고    scopus 로고
    • 4 + H, 329.1747; found, 329.1749.
    • 4 + H, 329.1747; found, 329.1749.
  • 12
    • 58149311564 scopus 로고    scopus 로고
    • Based on the chiral HPLC analysis against the corresponding racemic sample prepared under the same dihydroxylation condition without the chiral auxiliary, the desired enantiomer was formed exclusively
    • Based on the chiral HPLC analysis against the corresponding racemic sample prepared under the same dihydroxylation condition without the chiral auxiliary, the desired enantiomer was formed exclusively.
  • 13
    • 58149303355 scopus 로고    scopus 로고
    • 3a (see Supporting Information).
    • 3a (see Supporting Information).
  • 14
    • 58149277819 scopus 로고    scopus 로고
    • 3 etherate. With all four diastereomers available, chiral HPLC analyses concluded that only the benzylic center was epimerized.
    • 3 etherate. With all four diastereomers available, chiral HPLC analyses concluded that only the benzylic center was epimerized.
  • 22
    • 58149314641 scopus 로고    scopus 로고
    • A full conformational search was used Macromodel and MMFF94S forcefield, with 5000 steps of PRCG minimization for each conformation (or until completion, if that occurs sooner). There is a slight potential energy advantage to the (11aR,3aR,5R)-3 isomer as compared to the (11aR,3aR,5S)-3 isomer (310 vs 318 kJ/mol, respectively).
    • A full conformational search was used Macromodel and MMFF94S forcefield, with 5000 steps of PRCG minimization for each conformation (or until completion, if that occurs sooner). There is a slight potential energy advantage to the (11aR,3aR,5R)-3 isomer as compared to the (11aR,3aR,5S)-3 isomer (310 vs 318 kJ/mol, respectively).
  • 23
    • 58149303356 scopus 로고    scopus 로고
    • Reviewed in: Larghi, E. L.; Kaufman, T. S. Synthesis 2006, 2, 187-220.
    • Reviewed in: Larghi, E. L.; Kaufman, T. S. Synthesis 2006, 2, 187-220.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.