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Volumn 12, Issue 8, 2010, Pages 1760-1763

Tandem phenolic oxidative amidation-intramolecular diels-alder reaction: An approach to the himandrine core

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; FUSED HETEROCYCLIC RINGS; HIMANDRINE; PHENOL;

EID: 77951203347     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1003669     Document Type: Article
Times cited : (50)

References (62)
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    • Isolation
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    • Bioactivity
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    • Structural work
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    • Synthetic studies
    • Synthetic studies
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    • Total synthesis
    • Total synthesis
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    • Key reviews
    • Key reviews
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    • Prepared as detailed in the Supporting Information
    • Prepared as detailed in the Supporting Information.
  • 37
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    • This method furnishes a mixture of trans - and cis -isomers. Remarkably, these were chromatographically separable with only modest losses (see the Supporting Information)
    • This method furnishes a mixture of trans-and cis -isomers. Remarkably, these were chromatographically separable with only modest losses (see the Supporting Information).
  • 38
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    • For the first example of ortho -oxidative amidation of phenols see
    • For the first example of ortho -oxidative amidation of phenols see
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    • Dissertation, University Claude Bernard Lyon 1.
    • Canesi, S. Dissertation, University Claude Bernard Lyon 1, 2004.
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    • Canesi, S.1
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    • For a similar reaction see
    • For a similar reaction see
  • 42
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    • The structure of 20 is published
    • The structure of 20 is published
  • 48
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    • Prepared in situ by reaction of the acetylene with EtMgBr in THF.
    • Prepared in situ by reaction of the acetylene with EtMgBr in THF.
  • 50
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    • It should be noted that: (i) The acetylenic Grignard was superior to the lithium variant in the addition reaction. (ii) Lindlar hydrogenation [;, ()
    • It should be noted that: (i) The acetylenic Grignard was superior to the lithium variant in the addition reaction. (ii) Lindlar hydrogenation [ Lindlar, H.; Dubuis, R. Org. Synth. 1973, 5 (Collect.) 880
    • (1973) Org. Synth. , vol.5 , Issue.COLLECT. , pp. 880
    • Lindlar, H.1    Dubuis, R.2
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    • Of the alkyne failed, presumably on steric grounds. Thus, attempted Lindlar hydrogenation of 23 resulted in exclusive reduction of the olefin -(iii) Schwartz hydrozirconation [
    • Lindlar, H. Helv. Chim. Acta 1952, 35, 446 ] of the alkyne failed, presumably on steric grounds. Thus, attempted Lindlar hydrogenation of 23 resulted in exclusive reduction of the olefin -(iii) Schwartz hydrozirconation [
    • (1952) Helv. Chim. Acta , vol.35 , pp. 446
    • Lindlar, H.1
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    • Of the ethynyl group also failed; (iv) the configuration of 23 was ascertained by NOESY spectroscopy
    • Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115 ] of the ethynyl group also failed; (iv) the configuration of 23 was ascertained by NOESY spectroscopy
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 8115
    • Hart, D.W.1    Schwartz, J.2
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    • Deprotonation of the OH group was effected with KH, NaH, or KHMDS, with and without 18-crown-6, in benzene, toluene, THF, and DMSO
    • Deprotonation of the OH group was effected with KH, NaH, or KHMDS, with and without 18-crown-6, in benzene, toluene, THF, and DMSO.
  • 58
    • 77951160026 scopus 로고    scopus 로고
    • The conversion of 29 into 30 reflects an unprecedented mode of reactivity. However, related Diels-Alder reactions of quinone monoketal cognates of 29 are documented
    • The conversion of 29 into 30 reflects an unprecedented mode of reactivity. However, related Diels-Alder reactions of quinone monoketal cognates of 29 are documented
  • 62
    • 77951202342 scopus 로고    scopus 로고
    • Available from commercial homotyrosine as detailed in ref. 5.
    • Available from commercial homotyrosine as detailed in ref. 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.