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Volumn 38, Issue 13-14, 1999, Pages 1985-1986

A formal asymmetric synthesis of (+)-anatoxin-a using an enantioselective deprotonation strategy on an eight-membered ring

Author keywords

Anatoxin; Enantioselective deprotonation; Natural products; Total synthesis

Indexed keywords

ANATOXIN A;

EID: 0033549543     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990712)38:13/14<1985::aid-anie1985>3.0.co;2-7     Document Type: Article
Times cited : (51)

References (22)
  • 3
    • 0029914328 scopus 로고    scopus 로고
    • For a review of recent total syntheses of anatoxin-a, see H. L. Mansell, Tetrahedron 1996, 52, 6025.
    • (1996) Tetrahedron , vol.52 , pp. 6025
    • Mansell, H.L.1
  • 8
    • 0000414401 scopus 로고    scopus 로고
    • In the course of our work an enantioselective deprotonation of an eight-membered ring was reported. See W. F. Berkowitz, Y. Wu, J. Org. Chem. 1997, 62, 1536.
    • (1997) J. Org. Chem. , vol.62 , pp. 1536
    • Berkowitz, W.F.1    Wu, Y.2
  • 12
    • 0029026296 scopus 로고
    • Newcombe and Simpkins have described an asymmetric synthesis of (-)-anatoxin-a with an enantioselective deprotonation of a tropanone. See N. J. Newcombe, N. S. Simpkins, J. Chem. Soc. Chem. Commun. 1995, 831.
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 831
    • Newcombe, N.J.1    Simpkins, N.S.2
  • 13
    • 0344932522 scopus 로고    scopus 로고
    • note
    • Abbreviations: AcOH = acetic acid; Bn = benzyl; Boc = terr-butoxycarbonyl; p-TsOH = para-toluenesulfonic acid; PDC = pyridinium dichromate ; Tf = trifluoromethanesulfonyl; THF = tetrahydrofuran; Z = benzyloxycarbonyl.
  • 14
    • 0011863061 scopus 로고
    • For the synthesis of the N-methyl analogue of hemiaminal 8, see J. R. Wiseman, S. Y. Lee, J. Org. Chem. 1986, 51, 2485.
    • (1986) J. Org. Chem. , vol.51 , pp. 2485
    • Wiseman, J.R.1    Lee, S.Y.2
  • 20
    • 0344501541 scopus 로고    scopus 로고
    • note
    • The enantiomeric excess was determined by HPLC analysis on a Chiralcel OD column (hexane:iPrOH 98:2). Retention times: (R)-11: 16.8 min, (S)-11: 18.7 min.
  • 22
    • 85087232121 scopus 로고    scopus 로고
    • note
    • [4]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.