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Volumn 8, Issue 18, 2006, Pages 3999-4002

Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; IMINE; MARTINELLIC ACID; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE;

EID: 33748936678     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061473z     Document Type: Article
Times cited : (69)

References (39)
  • 1
    • 2942549122 scopus 로고    scopus 로고
    • and references therein
    • Katritzky, A. R. Chem. Rev. 2004, 104, 2125-2126 and references therein.
    • (2004) Chem. Rev. , vol.104 , pp. 2125-2126
    • Katritzky, A.R.1
  • 12
    • 0020046030 scopus 로고
    • Anhydride 18 was purchased from Sigma-Aldrich. Anhydrides 16, 17, 19, and 20 were synthesized by reported methods, with minor modifications (see Supporting Information). 16: (a) Barton, D. H. R.; Benechie, M.; Khuong-Huu, F., Potier, P.; Reyna-Pinedo, V. Tetrahedron Lett. 1982, 23, 651-654.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 651-654
    • Barton, D.H.R.1    Benechie, M.2    Khuong-Huu, F.3    Potier, P.4    Reyna-Pinedo, V.5
  • 17
    • 33748920081 scopus 로고    scopus 로고
    • note
    • The relative configuration of this compound was proven by conversion to the p-methoxyphenethyl amide and NOE spectroscopy. See Supporting Information.
  • 24
    • 33748951820 scopus 로고    scopus 로고
    • note
    • We have attempted a reaction between the benzylimine of pentafluorobenzaldehyde and anhydride 20, which was expected to give the lactam product with reduced diastereoselectivity. No conversion was observed, possibly due to reduced basicity of the imine nitrogen.
  • 26
    • 0035850304 scopus 로고    scopus 로고
    • Enantioselective synthesis of martinellic acid: (a) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189-2191.
    • (2001) Org. Lett. , vol.3 , pp. 2189-2191
    • Ma, D.1    Xia, C.2    Jiang, J.3    Zhang, J.4
  • 27
    • 0035961042 scopus 로고    scopus 로고
    • Syntheses of racemic martinellic acid and martinelline: (b) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217-4220.
    • (2001) Org. Lett. , vol.3 , pp. 4217-4220
    • Snider, B.B.1    Ahn, Y.2    O'Hare, S.M.3
  • 38
    • 33748940841 scopus 로고    scopus 로고
    • note
    • See Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.