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Volumn 71, Issue 2, 2006, Pages 593-605

Tandem double-intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. Studies toward a total synthesis of daphnilactone B: Piperidine ring construction

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; KETONES; NATURAL POLYMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 30744466920     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052001l     Document Type: Article
Times cited : (88)

References (62)
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    • University of Illinois, Urbana
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    • (2002) Postdoctoral Report
    • Gomez, L.1
  • 11
    • 77957053597 scopus 로고
    • Daphniphyllum alkaloids
    • Brossi, A., Ed.; Academic Press: Orlando
    • Yamamura, S. Daphniphyllum Alkaloids. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: Orlando, 1986; pp 265-286.
    • (1986) The Alkaloids: Chemistry and Pharmacology , pp. 265-286
    • Yamamura, S.1
  • 17
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    • note
    • 4 + H, 282.1705, found 282.1707).
  • 21
    • 30744445660 scopus 로고    scopus 로고
    • note
    • Calculations were performed using a Cache Worksystem Pro Version 6.1.12.33 software from Fujitsu Limited.
  • 25
    • 30744435563 scopus 로고    scopus 로고
    • note
    • MAD: methyl(bis(2,6-di-tert-butyl-4-methylphenoxy))aluminum; MAPh: methyl(bis(2,6-diphenylphenoxy))aluminum.
  • 27
    • 30744449932 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Illinois at Urbana-Champaign
    • Hurd, A. R. Ph.D. Thesis, University of Illinois at Urbana-Champaign, 2000.
    • (2000)
    • Hurd, A.R.1
  • 28
    • 30744469823 scopus 로고    scopus 로고
    • note
    • The relative configurations of 30a und 30b were not determined because this route was abandoned.
  • 33
    • 0042449862 scopus 로고
    • Alkyne carbocupration and polyene synthesis
    • Taylor, R. J. K., Ed.; Oxford University Press: New York
    • (b) Normant, J. F. Alkyne carbocupration and polyene synthesis. In Organocopper reagents, A practical approach; Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994.
    • (1994) Organocopper Reagents, A Practical Approach
    • Normant, J.F.1
  • 39
    • 30744470083 scopus 로고    scopus 로고
    • note
    • Nitroblefin 26 was formed as a mixture of isomers at the unsaturated ester double bond (E/Z ∼ 20/1). It is possible that the cycloaddition of 26 was completely stereoselective and the 20/1 ratio of the diastereometric nitroso acetals reflects the presence of the two isomers in the starting material. In this case, the minor cycloadduct may be the epimer of 38a at the ester-group-bearing stereocenter.
  • 40
    • 30744446183 scopus 로고    scopus 로고
    • note
    • The crystallographic coordinates of 38a have been deposited with the Cambridge Crystallographic Data Centre: deposition no. CCDC 275186. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Rond, Cambridge CB2 IEZ, UK.; fax: (4-44) 1223-336-033; or deposit@ccdc.cam.ac.uk). For the Chem3D image, see the Supporting Information.
  • 56
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    • Ph.D. Thesis, University of Illinois, Urbana
    • Moon, Y.-C. Ph.D. Thesis, University of Illinois, Urbana, 1991.
    • (1991)
    • Moon, Y.-C.1
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    • note
    • For a summary of recent strained and troublesome lactamizations, see ref 4.
  • 59
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    • note
    • In each case, to locate the saddle point, an energy surface map was calculated in the gas phase starting with the corresponding nitronate (bound to a molecule of trimethylaluminum) and systematically varying the C-C and N-O bond length. Frequency calculations were used to confirm the nature of the saddle points. All transition structures had only one imaginary frequency corresponding to the formation of the expected bonds. Reaction coordinate calculations were performed to determine the connections of the cycloaddition transition structures with the reactants and the products.
  • 60
    • 20544433165 scopus 로고
    • van der Waals radius of hydrogen is 1.20 Å (Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
    • (1964) J. Phys. Chem. , vol.68 , pp. 441-451
    • Bondi, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.