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Volumn 76, Issue 8, 2011, Pages 2494-2501

Protecting-group-free synthesis of chokols

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE; ENANTIOPURE; EXPERIMENTAL STUDIES; NATURAL PRODUCTS; STEREO-SELECTIVE; TEMPLATE EFFECTS; TWO-STEP PROTOCOL;

EID: 79953879675     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102280n     Document Type: Article
Times cited : (24)

References (52)
  • 1
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    • Examples of terpenoids containing in their structure a cyclopentane core with contiguous asymmetric centers
    • Examples of terpenoids containing in their structure a cyclopentane core with contiguous asymmetric centers: Rossinone, B; Appleton, D. R.; Chuen, C. S.; Berridge, M. V.; Webb, V. L.; Copp, B. R. J. Org. Chem. 2006, 74, 9195-9198
    • (2006) J. Org. Chem. , vol.74 , pp. 9195-9198
    • Rossinone, B.1    Appleton, D.R.2    Chuen, C.S.3    Berridge, M.V.4    Webb, V.L.5    Copp, B.R.6
  • 18
    • 85004704421 scopus 로고
    • The preparation of racemic 1 has been previously reported as a mixture of diastereomers in eight steps
    • The preparation of racemic 1 has been previously reported as a mixture of diastereomers in eight steps: Tanimori, S.; Ueda, T.; Nakayama, M. Biosci. Biotechnol. Biochem. 1993, 57, 1713-1715
    • (1993) Biosci. Biotechnol. Biochem. , vol.57 , pp. 1713-1715
    • Tanimori, S.1    Ueda, T.2    Nakayama, M.3
  • 20
    • 33845280764 scopus 로고
    • For pioneering work in this field, see
    • For pioneering work in this field, see: Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561-8562
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 8561-8562
    • Nugent, W.A.1    Rajanbabu, T.V.2
  • 37
    • 79953885994 scopus 로고    scopus 로고
    • Diastereoselective epoxide openings were already described by Nugent and RajanBabu, including cases with functionalized carbohydrate-derived epoxyalkenes; see ref 6d
    • Diastereoselective epoxide openings were already described by Nugent and RajanBabu, including cases with functionalized carbohydrate-derived epoxyalkenes; see ref 6d.
  • 41
    • 79953868083 scopus 로고    scopus 로고
    • note
    • Acyclic radicals Ia-d should be considered as conformers since according to the theoretical data the geometry of the carbon where the radical is located is trigonal (note that the x, y, and z Cartesian coordinates for all theoretically calculated species are provided in Supporting Information). On the other hand, the cyclic radicals IIa-d resulting from the cyclization (two stereocenters are created) are diastereomers.
  • 44
    • 79953900629 scopus 로고    scopus 로고
    • note
    • When 3a and 3b were subjected separately to the reaction conditions, the same mixture of products were obtained. Consequently, a balance between the axially and equatorially disposed radicals initially generated in each case should occur via a planar structure where the electron would be located in a p orbital. The theoretically calculated planar or quasi-planar disposition of the corresponding carbon in the acyclic radicals Ia-d supports this hypothesis.
  • 45
    • 85007976342 scopus 로고
    • Chemical conversions of chokol G to chokol K and chokol B, the latter as a mixture of diastereoisomers, has been previously reported
    • Chemical conversions of chokol G to chokol K and chokol B, the latter as a mixture of diastereoisomers, has been previously reported: Tanimori, S.; Ueda, T.; Nakayama, M. Biosci. Biotechnol. Biochem. 1994, 58, 1174-1176
    • (1994) Biosci. Biotechnol. Biochem. , vol.58 , pp. 1174-1176
    • Tanimori, S.1    Ueda, T.2    Nakayama, M.3
  • 46
    • 67650984682 scopus 로고    scopus 로고
    • For a review on this subject, see
    • For a review on this subject, see: Young, I. S.; Baran, P. S. Nature 2009, 1, 193-205
    • (2009) Nature , vol.1 , pp. 193-205
    • Young, I.S.1    Baran, P.S.2
  • 47
    • 33748677051 scopus 로고    scopus 로고
    • For previous synthetic reports on this type of compounds, see ref 1. The last synthesis of chokols reported was the Groth asymmetric preparation of chokol A:;;,. The overall yield of this convergent approach was 27% over 6 steps, starting from a chiral ester and a high order cuprate, which in turn were prepared in 3 and 5 steps, respectively
    • For previous synthetic reports on this type of compounds, see ref 1. The last synthesis of chokols reported was the Groth asymmetric preparation of chokol A: Groth, U.; Kesenheimer, C; Kreye, P. Synlett 2006, 2223-2226. The overall yield of this convergent approach was 27% over 6 steps, starting from a chiral ester and a high order cuprate, which in turn were prepared in 3 and 5 steps, respectively
    • (2006) Synlett , pp. 2223-2226
    • Groth, U.1    Kesenheimer, C.2    Kreye, P.3
  • 48
    • 79953840061 scopus 로고    scopus 로고
    • (+)-Nerolidol can be obtained directly in multigram quantities from Inula viscosa. For details see the Experimental Section
    • (+)-Nerolidol can be obtained directly in multigram quantities from Inula viscosa. For details see the Experimental Section.
  • 52
    • 0025634548 scopus 로고
    • The optical rotatory power of our (+)-natural compound (+12.2°) is comparable to that of (-)-nerolidol (-12.5°) obtained synthetically from (-)-linalool:;;;;,. These values suggest a high optical richness for our (+)-nerolidol
    • The optical rotatory power of our (+)-natural compound (+12.2°) is comparable to that of (-)-nerolidol (-12.5°) obtained synthetically from (-)-linalool: David, E.; Cane, D. E.; Ha, H.-J.; McIlwaine, D: B.; Pascoe, K. O. Tetrahedron Lett. 1990, 31, 7553-7554. These values suggest a high optical richness for our (+)-nerolidol
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7553-7554
    • David, E.1    Cane, D.E.2    Ha, H.-J.3    McIlwaine, D.B.4    Pascoe, K.O.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.