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Volumn 70, Issue 24, 2005, Pages 10004-10012

Synthesis of HKI 0231B

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; KETONES; NEGATIVE IONS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 28044436731     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051762l     Document Type: Article
Times cited : (31)

References (69)
  • 9
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    • note
    • 2, further substitution occurred in the 8-position.
  • 10
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    • note
    • 2 proved difficult and time-consuming on a large scale.
  • 14
    • 28044467188 scopus 로고    scopus 로고
    • note
    • 3N or Hunig's base led to acylation at the phenol. Schotten-Baumann conditions also proved ineffective in completing this transformation.
  • 22
    • 0003961355 scopus 로고    scopus 로고
    • Regioselective synthesis of organolithiums by deprotonation
    • Tetrahedron Organic Chemistry Series; Elsevier Science: London, Chapt. 2
    • (a) Clayden, J. Regioselective Synthesis of Organolithiums by Deprotonation. In Organolithiums: Selectivity for Synthesis; Tetrahedron Organic Chemistry Series; Elsevier Science: London, 2002; Vol. 23, Chapt. 2, pp 30-31.
    • (2002) Organolithiums: Selectivity for Synthesis , vol.23 , pp. 30-31
    • Clayden, J.1
  • 25
    • 28044450453 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum.
  • 28
    • 28044462260 scopus 로고    scopus 로고
    • note
    • Only silyl-based protecting groups could be successfully introduced on the phenol after the bromination reaction. Various benzyl groups were attempted, but all led to either recovered starting material or low yields.
  • 29
    • 28044440741 scopus 로고    scopus 로고
    • note
    • 2O and deuterium failed to incorporate into the ring system.
  • 30
    • 0011787127 scopus 로고
    • For other examples of where this has been necessary, see: (a) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7072
    • Kelly, T.R.1    Kim, M.H.2
  • 32
    • 0003961355 scopus 로고    scopus 로고
    • Regioselective synthesis of organolithiums by X-Li exchange
    • Tetrahedron Organic Chemistry Series; Elsevier Science: London, Chapt. 3
    • For a discussion on the kinetics of halogen-lithium exchange, see: Clayden, J. Regioselective Synthesis of Organolithiums by X-Li Exchange. In Organolithiums: Selectivity for Synthesis; Tetrahedron Organic Chemistry Series; Elsevier Science: London, 2002; Chapt. 3, pp 116-117.
    • (2002) Organolithiums: Selectivity for Synthesis , pp. 116-117
    • Clayden, J.1
  • 33
    • 28044453798 scopus 로고
    • Rearrangement reactions with migration of silicon
    • Butterworth Monographs in Chemistry and Chemical Engineering; Butterworth: London
    • For discussions of silicon group migrations, see: (a) Colvin, E. Rearrangement reactions with migration of silicon. In Silicon in Organic Synthesis; Butterworth Monographs in Chemistry and Chemical Engineering; Butterworth: London, 1981; pp 30-39.
    • (1981) Silicon in Organic Synthesis , pp. 30-39
    • Colvin, E.1
  • 35
    • 0003961355 scopus 로고    scopus 로고
    • Organolithium rearrangements
    • Tetrahedron Organic Chemistry Series; Elsevier Science: London, Chapt. 8
    • (c) Clayden, J. Organolithium Rearrangements. In Organolithiums: Selectivity for Synthesis; Tetrahedron Organic Chemistry Series; Elsevier Science: London, 2002; Chapt. 8, pp 340-346.
    • (2002) Organolithiums: Selectivity for Synthesis , pp. 340-346
    • Clayden, J.1
  • 37
    • 28044434472 scopus 로고    scopus 로고
    • note
    • This temperature is extremely important for the success of the transformation. Running the reaction at slightly higher (0 °C) or lower (-20 °C) temperatures resulted in incomplete lithiation.
  • 38
    • 28044435674 scopus 로고    scopus 로고
    • note
    • Presumably due to the base-induced decomposition of ethyl formate, DMF (when used as the aldehyde source), or THF.
  • 40
    • 6244279150 scopus 로고
    • For discussions and examples where TMSC1 has been used to accelerate the conjugate addition of organocopper and organocuprate reagents, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 6015
    • Corey, E.J.1    Boaz, N.W.2
  • 47
    • 28044460653 scopus 로고    scopus 로고
    • note
    • Running this reaction in DMF, DMSO, or THF resulted in only recovered starting material.
  • 57
    • 28044446830 scopus 로고    scopus 로고
    • note
    • Inferior yields were obtained with LiOH, NaOH, or CsOH. The use of other alcohols (i.e., EtOH, 'PrOH, "BuOH) as solvent also resulted in a reduction in yield.
  • 58
    • 28044450935 scopus 로고    scopus 로고
    • note
    • All attempts at applying the chemistry that afforded 11 to desmethyl derivatives of 59 were met with failure.
  • 63
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    • For related transformations that result in amide cleavage, see: (a) Charette, A. B.; Chua, P. Synlett 1998, 163.
    • (1998) Synlett , pp. 163
    • Charette, A.B.1    Chua, P.2
  • 65
    • 28044455287 scopus 로고    scopus 로고
    • note
    • Attempts to isolate the immonium intermediate in dry form and then treat it with methoxide in MeOH also failed.
  • 68
    • 28044442784 scopus 로고    scopus 로고
    • note
    • See Supporting Information for general experimental procedures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.