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Volumn 14, Issue 23, 2008, Pages 6862-6865

A flexible, stereoselective approach to the decorated cis-hydrindane skeleton: Synthesis of the proposed structure of faurinone

Author keywords

Hydrindane; Natural products; Radicals; Samarium; Total synthesis

Indexed keywords

HYDRINDANE; NATURAL PRODUCTS; RADICALS; SAMARIUM; TOTAL SYNTHESIS;

EID: 53849093450     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800930     Document Type: Article
Times cited : (28)

References (43)
  • 1
    • 0038055611 scopus 로고    scopus 로고
    • For a review of metal-mediated radical reactions, see: a
    • For a review of metal-mediated radical reactions, see: a) A. Gansauer, H. Bluhm, Chem. Rev. 2000, 100, 2771.
    • (2000) Chem. Rev , vol.100 , pp. 2771
    • Gansauer, A.1    Bluhm, H.2
  • 2
    • 0010077452 scopus 로고    scopus 로고
    • 2 in organic synthesis, see: b G. A. Molander, Chem. Rev. 1992, 92, 29;
    • 2 in organic synthesis, see: b) G. A. Molander, Chem. Rev. 1992, 92, 29;
  • 37
    • 53849144851 scopus 로고    scopus 로고
    • CCDC-684740, CCDC-684741, CCDC-684742, CCDC-684744 and CCDC-684745 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Further information is available in the Supporting Information.
    • CCDC-684740, CCDC-684741, CCDC-684742, CCDC-684744 and CCDC-684745 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Further information is available in the Supporting Information.
  • 41
    • 33747808546 scopus 로고    scopus 로고
    • 4-Isopropylcyclohexenone could also be prepared in 94% yield from nopinone using the procedure of Mori: K. Mori, Tetrahedron: Asymmetry 2006, 17, 2133.
    • 4-Isopropylcyclohexenone could also be prepared in 94% yield from nopinone using the procedure of Mori: K. Mori, Tetrahedron: Asymmetry 2006, 17, 2133.
  • 42
    • 53849093961 scopus 로고    scopus 로고
    • The structure originally proposed for faurinone by Hikino et al. was revised by Bos et al, see ref, 4, While only partial spectroscopic data is available for the natural product, NMR data for synthetic 2 prepared during our studies does not match the partial, reported data in ref, 4, We have also prepared epi-2 from 31 TMSCH2Li, THF, 0°C, 77, epi-2 also does not match the partial reported data given in ref, 4
    • 2Li, THF, 0°C, 77%). epi-2 also does not match the partial reported data given in ref. [4].
  • 43
    • 0027323891 scopus 로고    scopus 로고
    • Access to enantiomerically-enriched 4-alkylcyclohexenones, using the approach of Koga et al., allows the asymmetric synthesis of cis-hydrindanes using our approach. K. Aoki, M. Nakajima, K. Tomioka, K. Koga, Chem. Pharm. Bull. 1993, 41, 994.
    • Access to enantiomerically-enriched 4-alkylcyclohexenones, using the approach of Koga et al., allows the asymmetric synthesis of cis-hydrindanes using our approach. K. Aoki, M. Nakajima, K. Tomioka, K. Koga, Chem. Pharm. Bull. 1993, 41, 994.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.