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Volumn 11, Issue 15, 2009, Pages 3178-3181

A concise diels-alder strategy for the asymmetric synthesis of (+)-albicanol, (+)-albicanyl acetate, (+)-dihydrodrimenin, and (-)-dihydroisodrimeninol

Author keywords

[No Author keywords available]

Indexed keywords

ALBICANOL; ALBICANYL ACETATE; ANTIINFECTIVE AGENT; DIHYDRODRIMENIN; DIHYDROISODRIMENINOL; NAPHTHALENE DERIVATIVE; SESQUITERPENE;

EID: 68149108486     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901372m     Document Type: Article
Times cited : (18)

References (41)
  • 7
    • 0029843081 scopus 로고    scopus 로고
    • To our knowledge, (-)-dihydro-isodrimeninol 4 has not been tested for biological activity: Montagnac, A.; Martin, M.-T.; Debitus, C.; Pais, M. J. Nat. Prod. 1996, 59, 866.
    • (d) To our knowledge, (-)-dihydro-isodrimeninol 4 has not been tested for biological activity: Montagnac, A.; Martin, M.-T.; Debitus, C.; Pais, M. J. Nat. Prod. 1996, 59, 866.
  • 20
    • 0031562127 scopus 로고    scopus 로고
    • 3, see: Mayelvaganan, T.; Hadimani, S. B.; Bhat, S. V. Tetrahedron 1997, 53, 2185.
    • 3, see: Mayelvaganan, T.; Hadimani, S. B.; Bhat, S. V. Tetrahedron 1997, 53, 2185.
  • 31
    • 0035925006 scopus 로고    scopus 로고
    • Diene 5 was easily prepared from β-ionone by oxzonolysis followed by a Peterson olefination. For details, see: (a) Crombie, B. S.; Smith, C.; Varnavas, C Z.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 2001, 206.
    • Diene 5 was easily prepared from β-ionone by oxzonolysis followed by a Peterson olefination. For details, see: (a) Crombie, B. S.; Smith, C.; Varnavas, C Z.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 2001, 206.
  • 33
    • 68149151644 scopus 로고    scopus 로고
    • w = 0.0977.
    • w = 0.0977.
  • 34
    • 0037007705 scopus 로고    scopus 로고
    • 2 with acyclic (Z)-1,3-dienes using N-acryloyl sultam as a chiral auxiliary. (a) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002,4, 1543.
    • 2 with acyclic (Z)-1,3-dienes using N-acryloyl sultam as a chiral auxiliary. (a) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002,4, 1543.
  • 35
    • 68149107062 scopus 로고    scopus 로고
    • Interestingly, a similar reaction with an achiral oxazolidinone did not provide any DA products, see
    • Interestingly, a similar reaction with an achiral oxazolidinone did not provide any DA products, see:
  • 37
    • 68149154124 scopus 로고    scopus 로고
    • 3 was used (DCM, 5 h, rt).
    • 3 was used (DCM, 5 h, rt).
  • 39
    • 68149176025 scopus 로고    scopus 로고
    • 1H NMR spectrum with a few very minor unidentified compounds. After 18 h, the endo isomer could not be detected in the NMR spectrum. See the Supporting Information for more details.
    • 1H NMR spectrum with a few very minor unidentified compounds. After 18 h, the endo isomer could not be detected in the NMR spectrum. See the Supporting Information for more details.
  • 40
    • 68149143589 scopus 로고    scopus 로고
    • The structure of 18 was confirmed by X-ray crystal structure analysis. See the Supporting Information section for more details.
    • The structure of 18 was confirmed by X-ray crystal structure analysis. See the Supporting Information section for more details.
  • 41
    • 68149109502 scopus 로고    scopus 로고
    • This reaction gave a 5:1 mixture of isomers that were epimeric at the ester in 20
    • This reaction gave a 5:1 mixture of isomers that were epimeric at the ester in 20.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.