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Volumn 48, Issue 50, 2007, Pages 8787-8789

Diastereoselective synthesis of the polyol-containing side chain of the ent-bengamides

Author keywords

Bengamides; Boron aldol reactions; Substrate controlled diastereoselectivity

Indexed keywords

BENGAMIDE DERIVATIVE; NATURAL PRODUCT; POLYOL; UNCLASSIFIED DRUG;

EID: 36048959282     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.083     Document Type: Article
Times cited : (5)

References (31)
  • 24
    • 0035477181 scopus 로고    scopus 로고
    • The current synthesis is applicable to the natural enantiomer of the bengamides as the antipode of ketone 1 (ent-1) is known:
    • The current synthesis is applicable to the natural enantiomer of the bengamides as the antipode of ketone 1 (ent-1) is known:. Forsyth C.J., Hao J., and Aiguadé J. Angew. Chem., Int. Ed. 40 (2001) 3663-3667
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3663-3667
    • Forsyth, C.J.1    Hao, J.2    Aiguadé, J.3
  • 25
    • 36049005790 scopus 로고    scopus 로고
    • note
    • 3N. Pure 6 could be obtained (as a mixture of diastereomers) by chromatography on Iatrobeads 6RS-8060, available from Mitsubishi Kagaku Iatron, Inc.
  • 27
    • 36048986566 scopus 로고    scopus 로고
    • note
    • The benzoate protecting groups, while not necessary for completion of the synthesis, are necessary to achieve the desired selectivity in the aldol reaction (see Ref. 4).
  • 28
    • 36049035788 scopus 로고    scopus 로고
    • note
    • For ease of isolation, an N-phenyl amide was selected for the current exercise but it is expected that a diverse array of amines could be used for this process, including caprolactam derivatives which would lead to the bengamide family.
  • 30
    • 36048988260 scopus 로고    scopus 로고
    • note
    • It is also likely that the alkoxide acts as a base in an intramolecular fashion, since recovered starting material is always diastereomerically pure.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.