메뉴 건너뛰기




Volumn 39, Issue 14, 2000, Pages 2533-2536

Asymmetric synthesis of phorboxazole B - Part I: Synthesis of the C20-C38 and C39-C46 subunits

Author keywords

Aldol reactions; Antitumor agents; Macrolides; Natural products; Total synthesis

Indexed keywords

PHORBOXAZOLE B;

EID: 0034679519     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2533::AID-ANIE2533>3.0.CO;2-B     Document Type: Article
Times cited : (78)

References (61)
  • 4
    • 0342829555 scopus 로고    scopus 로고
    • 50 is defined as the concentration at which cell growth is inhibited by 50%. See ref. [1a] and [1b]. Phorboxazoles A and B display comparable biological activities, see ref. [1a]
    • 50 is defined as the concentration at which cell growth is inhibited by 50%. See ref. [1a] and [1b]. Phorboxazoles A and B display comparable biological activities, see ref. [1a].
  • 26
    • 0001448377 scopus 로고    scopus 로고
    • D. A. Evans, D. M. Fitch, Angew. Chem. 2000, 112, 2636-2640; Angew. Chem. Int. Ed. 2000, 39, 2536-2540.
    • (2000) Angew. Chem. , vol.112 , pp. 2636-2640
    • Evans, D.A.1    Fitch, D.M.2
  • 27
    • 0034679493 scopus 로고    scopus 로고
    • D. A. Evans, D. M. Fitch, Angew. Chem. 2000, 112, 2636-2640; Angew. Chem. Int. Ed. 2000, 39, 2536-2540.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2536-2540
  • 28
    • 0343700041 scopus 로고    scopus 로고
    • note
    • Abbreviations: dr=diastereomer ratio; TES=triethylsilyl; TPS= triphenylsilyl; TIPS=triisopropylsilyl; Ms=methanesulfonyl; Bn= benzyl; TMS=trimethylsilyl; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene; DMF=N,N-dimethylformamide; DMAP=N,N-dimethylaminopyridine; LDA=lithium diisopropylamide; TMP=2,2,6,6-tetramethylpiperidide; NBS=N-bromosuccinimide; Tr=trityl=triphenylmethyl; Ts=para-toluenesulfonyl; DIAD=diisopropylazodicarboxylate; THF=tetrahydrofuran; HMDS=hexamethyldisilazide; pyr=pyridine; TEA=triethylamine; DMSO=dimethyl sulfoxide; Tf=triflate=trifluoromethanesulfonyl.
  • 33
    • 0343700039 scopus 로고    scopus 로고
    • note
    • 1 major=14.9min).
  • 37
    • 0342394803 scopus 로고    scopus 로고
    • 1H NMR analysis (500 MHz)
    • 1H NMR analysis (500 MHz).
  • 39
    • 84988093935 scopus 로고    scopus 로고
    • For similar conditions employing ethylene glycol in place of methanol, see a) T. H. Chan, M. A. Brook, T. Chaly, Synthesis 1983, 203-205; b) ref. [4].
    • (1983) Synthesis , pp. 203-205
    • Chan, T.H.1    Brook, M.A.2    Chaly, T.3
  • 40
    • 84988093935 scopus 로고    scopus 로고
    • ref. [4]
    • For similar conditions employing ethylene glycol in place of methanol, see a) T. H. Chan, M. A. Brook, T. Chaly, Synthesis 1983, 203-205; b) ref. [4].
  • 42
    • 0342394800 scopus 로고    scopus 로고
    • For reports of oxazole lithiation, see ref. [3h], and references therein
    • For reports of oxazole lithiation, see ref. [3h], and references therein.
  • 47
    • 0025312341 scopus 로고
    • (R)-3-(triphenylmethyl)-1,2-epoxypropane is commercially available from Aldrich Chemical Co. and may also be prepared in 95% ee by Sharpless asymmetric epoxidation of allyl alcohol and in situ tritylation. Recrystallization provides the enantiomerically enriched compound: H. S. Hendrickson, E. K. Hendrickson, Chem. Phys. Lipids 1990, 53, 115-120.
    • (1990) Chem. Phys. Lipids , vol.53 , pp. 115-120
    • Hendrickson, H.S.1    Hendrickson, E.K.2
  • 54
    • 0000730188 scopus 로고
    • M. T. Reetz, Angew. Chem. 1984, 96, 542-555; Angew. Chem. Int. Ed. Engl. 1984, 23, 556-569.
    • (1984) Angew. Chem. , vol.96 , pp. 542-555
    • Reetz, M.T.1
  • 55
    • 0010771837 scopus 로고
    • M. T. Reetz, Angew. Chem. 1984, 96, 542-555; Angew. Chem. Int. Ed. Engl. 1984, 23, 556-569.
    • (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 556-569
  • 56
    • 0342394795 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 57
    • 0026601825 scopus 로고
    • We are aware of few examples of this type of selective lithium-halogen exchange reaction. For a report involving bishalogenated arenes, see M. Kihara, M. Kashimoto, Y. Kohayashi, Tetrahedron 1992, 48, 67-78.
    • (1992) Tetrahedron , vol.48 , pp. 67-78
    • Kihara, M.1    Kashimoto, M.2    Kohayashi, Y.3
  • 58
    • 0032483753 scopus 로고    scopus 로고
    • For an example of a chelation-controlled zincate addition, see D. R. Williams, W. S. Kissel, J. Am. Chem. Soc. 1998, 120, 11198-11199.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11198-11199
    • Williams, D.R.1    Kissel, W.S.2
  • 60
    • 0001553338 scopus 로고
    • A similar solvent effect has been noted in additions of alkenyl Grignard reagents to α-alkoxyaldehydes: G. E. Keck, M. A. Andrus, D. R. Romer, J. Org. Chem. 1991, 56, 417-420.
    • (1991) J. Org. Chem. , vol.56 , pp. 417-420
    • Keck, G.E.1    Andrus, M.A.2    Romer, D.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.