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Volumn 47, Issue 17, 2008, Pages 3242-3244

Total synthesis of (+)-neopeltolide by a Prins macrocyclization

Author keywords

Antitumor agents; Cyclization; Macrocycles; Macrolides; Oxonium ions

Indexed keywords

CHEMICAL REACTIONS;

EID: 45549090228     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800386     Document Type: Article
Times cited : (115)

References (18)
  • 4
    • 37349010312 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 9211-9214.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 9211-9214
  • 8
    • 53549127984 scopus 로고    scopus 로고
    • In the synthesis of 1 by Scheidt and co-workers (reference [4, the intramolecular Prins cyclization of a dioxinone-containing precursor was catalyzed by Sc(OTf)3 25% yield
    • 3 (25% yield).
  • 13
    • 34248662084 scopus 로고    scopus 로고
    • Removal of the TBS group was accompanied by ethoxide elimination, and we decide to investigate the reactivity of 11 directly. Similar reaction conditions were adopted for free and silyl-protected homoallylic alcohols in the synthesis of blepharocalyxin D; H. M. Ko, D. G. Lee, M. A. Kim, H. J. Kim, J. Park, M. S. Lah, E. Lee, Tetrahedron 2007, 63, 5797-5805.
    • Removal of the TBS group was accompanied by ethoxide elimination, and we decide to investigate the reactivity of 11 directly. Similar reaction conditions were adopted for free and silyl-protected homoallylic alcohols in the synthesis of blepharocalyxin D; H. M. Ko, D. G. Lee, M. A. Kim, H. J. Kim, J. Park, M. S. Lah, E. Lee, Tetrahedron 2007, 63, 5797-5805.
  • 14
    • 33750041945 scopus 로고    scopus 로고
    • The minor product is presumably epimeric at C3, C5, and C7. For a thorough discussion of the racemization problem in the Prins cyclization, see: R. Jasti, S. D. Rychnovsky, J. Am. Chem. Soc. 2006, 128, 13640-13648.
    • The minor product is presumably epimeric at C3, C5, and C7. For a thorough discussion of the racemization problem in the Prins cyclization, see: R. Jasti, S. D. Rychnovsky, J. Am. Chem. Soc. 2006, 128, 13640-13648.
  • 16
    • 53549092412 scopus 로고    scopus 로고
    • In the NMR analysis, the presence of the racemization product was not detected
    • In the NMR analysis, the presence of the racemization product was not detected.
  • 17
    • 0037144093 scopus 로고    scopus 로고
    • Carboxylic acid 2 was prepared by using the known sequence with minor modifications: L. A. Dakin, N. F. Langille, J. S. Panek, J. Org. Chem. 2002, 67, 6812-6815.
    • Carboxylic acid 2 was prepared by using the known sequence with minor modifications: L. A. Dakin, N. F. Langille, J. S. Panek, J. Org. Chem. 2002, 67, 6812-6815.
  • 18
    • 53549109346 scopus 로고    scopus 로고
    • -3, MeOH).
    • -3, MeOH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.