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Volumn 128, Issue 4, 2006, Pages 1346-1352

Enantioselective syntheses of georgyone, arborone, and structural relatives. Relevance to the molecular-level understanding of olfaction

Author keywords

[No Author keywords available]

Indexed keywords

METHANOL; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; ODORS; PROTEINS; SYNTHESIS (CHEMICAL);

EID: 31944433641     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057483x     Document Type: Article
Times cited : (55)

References (60)
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    • Nobel lecture in physiology and medicine for 2004
    • (b) Buck, L. B. Nobel Lecture in Physiology and Medicine for 2004. Angew. Chem., Int. Ed. 2005, 44, 6128-6140 and www.nobel.se.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6128-6140
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    • Buck, L.B.1
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    • RSC Paperbacks, Royal Society of Chemistry: London
    • (a) Pybus, D. H.; Sell, C. S. The Chemistry of Odors; RSC Paperbacks, Royal Society of Chemistry: London, 1999.
    • (1999) The Chemistry of Odors
    • Pybus, D.H.1    Sell, C.S.2
  • 18
    • 31944440964 scopus 로고    scopus 로고
    • note
    • We are indebted to Dr. G. Fráter of Givaudan Dübendorf AG for a gift of racemic Georgywood.
  • 28
    • 31944446193 scopus 로고    scopus 로고
    • note
    • Although synthetic 1 was contaminated by about 10% of the (1S,2S)-diastereomer, there is no contribution of this impurity to odor since it is essentially odorless, as shown in a later section of this paper.
  • 29
    • 31944445855 scopus 로고    scopus 로고
    • note
    • Odor testing was carried out with several members of our research group, including the authors, with good agreement on the consensus evaluation of odor.
  • 34
    • 0345621603 scopus 로고    scopus 로고
    • Spectral data for (+)-(2) were in agreement with those reported for the racemate: Fráter, G.; Kraft, P. Helv. Chim. Acta 1999, 82, 1016.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 1016
    • Fráter, G.1    Kraft, P.2
  • 36
    • 31944445047 scopus 로고    scopus 로고
    • note
    • The Diels-Alder reaction can be carried out using an excess of the racemic diene 17 because of a faster rate of reaction for the (R)- vs the (S)-enantiomer, an interesting illustration of the efficacy of catalyst 5. This is an unusual example of kinetic resolution in a catalytic enantioselective Diels-Alder reaction.
  • 39
    • 31944443644 scopus 로고    scopus 로고
    • note
    • The results that are summarized in Scheme 7 also show that this particular Diels-Alder reaction is not useful for the synthesis of (+)-2, although we entertained this possibility when considering alternative synthetic routes to 2 that are simpler than the one set out in Scheme 2.
  • 40
    • 31944443533 scopus 로고    scopus 로고
    • note
    • For details of X-ray diffraction analysis of the tosylhydrazone of 38, see the Supporting Information.
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    • For a summary of older work on the possibility of multiple second messengers, see: Schild, D.; Restrepo, D. Physiol. Rev. 1998, 78, 429-466.
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  • 48
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    • note
    • This collaborative research by the authors. Prof. Meister and Mr. Edward Soucy, will be described in detail elsewhere.
  • 50
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    • note
    • Only about 20% of the mouse olfactory glomeruli are accessible for study using the optical analysis technique. It is thus possible that additional glomeruli are activated by olfactory ligands 1 and 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.