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Volumn , Issue 15, 2008, Pages 2267-2270

Molecular complexity from aromatics - An efficient route to 1,8-dimethyl-5-spirocyclopropanetricyclo[6.3.0.02,6]undec-10-one: A potential intermediate for synthesis of ceratopicanol

Author keywords

Cycloaddition; Diels Alder reaction; Oxa di pi methane rearrangement; Triquinanes

Indexed keywords

1,8 DIMETHYL 5 SPIROCYCLOPROPANETRICYCLO[6.3.0.0 2,6]UNDEC 10 ONE; CYCLOPROPANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 52949130968     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078592     Document Type: Article
Times cited : (8)

References (41)
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    • (a) Isolation: Hellwig, V.; Dasenbrock, J.; Schumann, S.; Steglich, W.; Leonhardt, K.; Anke, T. Eur. J. Org. Chem. 1998, 73.
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    • Synthesis of cucumin H: Srikrishna, A.; Dethe, D. H. Org. Lett. 2003, 5, 2295.
    • (b) Synthesis of cucumin H: Srikrishna, A.; Dethe, D. H. Org. Lett. 2003, 5, 2295.
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    • All compounds gave satisfactory spectral and analytical data. Analytical Data for Adduct 7 Mp 95-96°C. IR (film, νmax, 1731 cm-1. 1H NMR (300 MHz, CDCl 3, δ, 5.75 (d, J, 6.24 Hz, 1 H, 5.73-5.64 (m, 1 H, 5.49-5.44 (m, 1 H, 3.29-3.22 (m, 2 H, 3.02 (part of an AB pattern, J, 6.00 Hz, 1 H, 2.91 (part of AB pattern, J, 6.00 Hz, 1 H, 2.74 (superimposed ddd, J1, 9.75 Hz, J2, 4.17 Hz, 1 H, 2.54-2.45 (m, 1 H, 2.03-1.92 (m, 1 H, 1.75 (d, J, 1.56 Hz, 3 H, 1.06 (s, 3 H, 13C NMR 75 MHz, CDCl3, δ, 206.0, 144.0, 133.0, 129.0, 120.0, 59.3, 51.6, 49.2, 49.1, 44.5, 42.7, 36.5, 20.2, 12.7 ESI-HRMS: m/z calcd for C14H16O 2Na: 239.1048 [M, Na, Found: 239.1054 [M, Na
    • +.
  • 30
    • 52949107532 scopus 로고    scopus 로고
    • Analytical Data for Compound 13 Mp 98-99°C. IR (neat, νmax, 1736 cm-1. 1H NMR (300 MHz, CDCl 3, δ, 5.89 (d, J, 6.40 Hz, 1 H, 3.94-3.88 (m, 4 H, 2.97-2.94 (m, 1 H, 2.52 (dd, J1, 4.80 Hz, J 2, 2.40 Hz, 1H, 2.48-2.26 (m, 3 H, 1.96 (ddd, J1, 7.78 Hz, J2, 5.49 Hz, J3, 2.29 Hz, 1 H, 1.88-1.80 (m, 1 H, 1.77 (d, J, 1.37 Hz, 3 H, 1.63 (AB system, JAB, 13.90 Hz, 2 H, 1.11 (s, 3 H, 13C NMR 75 MHz, CDCl3, δ, 218.9, 145.0, 123.5, 112.6, 64.2, 64.0, 47.8, 44.9, 44.6, 42.7, 42.1, 40.7, 34.3, 21.1, 19.8. ESI-HRMS: m/z calcd for C15H21O3: 249.1491 [M, H, Found: 249.1490 [M, H, Crystal Data of 13 C15H 20O3, M248.31, space group, triclinic, P1, a, 7.1576
    • 2 = 0.1091. The complete crystal data can be obtained free of charge from The Cambridge Crystallographic data Centre via www.ccdc.cam.ac.uk/data_request/cif under the CCDC number 687727.
  • 31
    • 52949093839 scopus 로고    scopus 로고
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  • 33
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    • Padwa, A, Ed, Marcel Dekker: New York, and references cited therein
    • (b) Demuth, M. In Organic Photochemistry, Vol. 11; Padwa, A., Ed.; Marcel Dekker: New York, 1991, 37-97; and references cited therein.
    • (1991) Organic Photochemistry , vol.11 , pp. 37-97
    • Demuth, M.1
  • 37
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  • 40
    • 52949151848 scopus 로고    scopus 로고
    • Analytical Data for Compound 4 IR (neat, νmax, 1743 cm-1. 1H NMR (400 MHz, CDCl3, δ, 2.85-2.76 (m, 1 H, 2.56 (dd, J1, 18.33 Hz, J 2, 8.78 Hz, 1 H, 2.43-2.27 (m, 2 H, 2.18-2.06 (m, 2 H, 1.93 (dd, J1, 13.56 Hz, J2, 9.16 Hz, 1 H, 1.79 (dd, J1, 12.83 Hz, J2, 7.69 Hz, 1 H, 1.65 1.56 (m, 1 H, 1.55 1.47 (m, 2 H, 1.34 (dd, J1, 12.09 Hz, J2, 9.16 Hz, 1 H, 1.14 (s, 3 H, 1.03 (s, 3 H, 0.54 0.45 (m, 2 H, 0.34 0.28 (m, 2 H, 13C NMR 100 MHz, CDCl3, δ, 219.8, 55.4, 54.0, 52.2, 51.7, 49.5, 45.2, 43.4, 42.0, 37.3, 24.6, 23.8, 19.3, 12.7, 9.8. ESI-HRMS: m/z calcd for C15H 23O: 219.1749 [M, H, Found: 219.1744 [M, H
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.