메뉴 건너뛰기




Volumn 75, Issue 24, 2010, Pages 8465-8470

Total synthesis of (+)-cymbodiacetal: A re-evaluation of the biomimetic route

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOISOMERS; DIASTEREOMERIC; DIELS-ALDER CYCLOADDITIONS; HEMIACETALS; HETERO-DIELS-ALDER; LIMONENE OXIDE; OXIDATION REACTIONS; QUANTITATIVE YIELDS; RE-EVALUATION; TOTAL SYNTHESIS;

EID: 78650334308     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101691n     Document Type: Article
Times cited : (10)

References (20)
  • 3
    • 22244468033 scopus 로고    scopus 로고
    • For other spirochroman-containing natural products, see
    • For other spirochroman-containing natural products, see: Zhang, Y.; Lu, Y.; Mao, L.; Proksch, P.; Lin, W. Org. Lett. 2005, 7, 3037
    • (2005) Org. Lett. , vol.7 , pp. 3037
    • Zhang, Y.1    Lu, Y.2    Mao, L.3    Proksch, P.4    Lin, W.5
  • 11
    • 78650313509 scopus 로고    scopus 로고
    • However, upon standing for prolonged periods, the enone 3 completely dimerizes to form the spirochromans 2 and 7
    • However, upon standing for prolonged periods, the enone 3 completely dimerizes to form the spirochromans 2 and 7.
  • 12
    • 0000293463 scopus 로고
    • For background information regarding this type of hetero-Diels-Alder cycloaddition, see
    • For background information regarding this type of hetero-Diels-Alder cycloaddition, see: Desimoni, G.; Tacconi, G. Chem. Rev. 1975, 75, 651
    • (1975) Chem. Rev. , vol.75 , pp. 651
    • Desimoni, G.1    Tacconi, G.2
  • 13
    • 0040019740 scopus 로고
    • α,β-Unsaturated Carbonyl Compounds as Dienes
    • Ed.; Academic Press: New York
    • Colonge, J.; Descotes, G. α,β-Unsaturated Carbonyl Compounds as Dienes. In Organic Chemistry; Hamer, J., Ed.; Academic Press: New York, 1967; Vol. 8, pp 217 - 253.
    • (1967) Organic Chemistry , vol.8 , pp. 217-253
    • Colonge, J.1    Descotes, G.2    Hamer, J.3
  • 14
    • 0032499086 scopus 로고    scopus 로고
    • Hetero-Diels-Alder cycloadditions of this type are reported to be endo -selective
    • Hetero-Diels-Alder cycloadditions of this type are reported to be endo -selective: Hosoyama, H.; Shigemori, H.; In, Y.; Ishida, T.; Kobayashi, J. Tetrahedron Lett. 1998, 39, 2159
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2159
    • Hosoyama, H.1    Shigemori, H.2    In, Y.3    Ishida, T.4    Kobayashi, J.5
  • 15
    • 0001754618 scopus 로고
    • For a description of the Alder endo -rule, see
    • For a description of the Alder endo -rule, see: Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510
    • (1937) Angew. Chem. , vol.50 , pp. 510
    • Alder, K.1    Stein, G.2
  • 16
    • 78650349450 scopus 로고    scopus 로고
    • It has been reported that PCC can perform epoxidations (see ref 11). It is therefore possible that 2 is being oxidized in situ to produce 14 (or closely related species), which then reacts further under the acidic reaction conditions to produce 1
    • It has been reported that PCC can perform epoxidations (see ref 11). It is therefore possible that 2 is being oxidized in situ to produce 14 (or closely related species), which then reacts further under the acidic reaction conditions to produce 1.
  • 19
    • 78650342909 scopus 로고    scopus 로고
    • 2O) leads to identical results, and the two methods can be used interchangeably
    • 2O) leads to identical results, and the two methods can be used interchangeably.
  • 20
    • 78650377556 scopus 로고    scopus 로고
    • The crystallographic data have been deposited with the Cambridge Crystallographic Data Centre. CCDC 790825 contains the supplementary crystallographic data for 1, CCDC 790826 contains the supplementary crystallographic data for 8, CCDC 790827 contains the supplementary crystallographic data for 9, and CCDC 790828 contains the supplementary crystallographic data for 16. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via
    • The crystallographic data have been deposited with the Cambridge Crystallographic Data Centre. CCDC 790825 contains the supplementary crystallographic data for 1, CCDC 790826 contains the supplementary crystallographic data for 8, CCDC 790827 contains the supplementary crystallographic data for 9, and CCDC 790828 contains the supplementary crystallographic data for 16. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.